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864771-44-8

864771-44-8 Structure

864771-44-8 Structure
IdentificationBack Directory
[Name]

TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDAZOLE-1-CARBOXYLATE
[CAS]

864771-44-8
[Synonyms]

2-(1-Bo
864771-44-8
1-Boc-indazole-5-boronic acid pinacol ester
1-Boc-indazolyl-5-boronic Acid Pinacol Ester
1-Boc-1H-indalzole-5-boronic acid picol ester
1-Boc-1H-indalzole-5-boronic acid pinacol ester
1H-Indazole-5-boronic acid pinacol ester, N1-BOC protected
1-(tert-Butoxycarbonyl)indazolyl-5-boronic Acid Pinacol Ester
1-Boc-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)indazole
1-(tert-Butoxycarbonyl)-1H-indazole-5-boronic acid pinacol ester
1-Boc-5-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole
tert-butyl 5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate
2-(1-tert-Butoxycarbonyl-5-indazolyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1-Boc-5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)indazole, contains isomer
tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole-1-carboxyla
1-(tert-Butoxycarbonyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)indazole
tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indazole-1-carboxylate
tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate
tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate
5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)- indazole-1-carboxylic acid tert-butyl ester
1H-Indazole-1-carboxylicacid,5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-,1,1-diMethylethylester
tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate, 1-(tert-Butoxycarbonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole
[Molecular Formula]

C18H25BN2O4
[MDL Number]

MFCD08437629
[MOL File]

864771-44-8.mol
[Molecular Weight]

344.213
Chemical PropertiesBack Directory
[Melting point ]

110 °C
[Boiling point ]

461.4±37.0 °C(Predicted)
[density ]

1.13±0.1 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[form ]

solid
[pka]

-1.48±0.30(Predicted)
[Appearance]

White to off-white Solid
[InChI]

1S/C18H25BN2O4/c1-16(2,3)23-15(22)21-14-9-8-13(10-12(14)11-20-21)19-24-17(4,5)18(6,7)25-19/h8-11H,1-7H3
[InChIKey]

MMXDKXUKSKMROG-UHFFFAOYSA-N
[SMILES]

CC1(C)C(C)(C)OB(C2=CC=C3N(C(OC(C)(C)C)=O)N=CC3=C2)O1
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P280-P305+P351+P338
[Hazard Codes ]

Xn
[Risk Statements ]

22-36/37/38
[Safety Statements ]

22-26-36/37/39
[WGK Germany ]

WGK 3
[HS Code ]

2933998090
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Spectrum DetailBack Directory
[Spectrum Detail]

TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDAZOLE-1-CARBOXYLATE(864771-44-8)1HNMR
Hazard InformationBack Directory
[Synthesis]

TERT-BUTYL 5-BROMO-1H-INDAZOLE-1-CARBOXYLATE

651780-02-8

Bis(pinacolato)diboron

73183-34-3

TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDAZOLE-1-CARBOXYLATE

864771-44-8

Tert-butyl 5-bromo-1H-indazole-1-carboxylate (10.1 mmol) and pinacol ester of bisboronic acid (11.1 mmol) were used as raw materials for the reaction catalyzed by palladium(II) acetate (1.01 mmol) and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) (1.01 mmol) with the addition of potassium acetate (30.3 mmol) in triethylamine ( 1.5 mL) solution of potassium acetate (30.3 mmol) and 1,4-dioxane (60 mL) as a solvent, and the reaction was carried out at 110 °C overnight. After completion of the reaction, the mixture was concentrated under reduced pressure and the residue was purified by fast column chromatography (eluent: 5% ethyl acetate/petroleum ether) to afford the target product 1-tert-butoxycarbonylindazole-5-boronic acid pinacol ester as a yellow solid in 74% yield.

[References]

[1] Patent: WO2011/66211, 2011, A1. Location in patent: Page/Page column 69-70
[2] Organic Letters, 2009, vol. 11, # 13, p. 2860 - 2863
[3] Patent: WO2010/59943, 2010, A2. Location in patent: Page/Page column 83; 84
[4] Patent: WO2006/86705, 2006, A1. Location in patent: Page/Page column 89
[5] Patent: US2008/153813, 2008, A1. Location in patent: Page/Page column 22
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