methyl 4-(indol-3-yl)butyrate synthesis

8synthesis methods

Product Name:methyl 4-(indol-3-yl)butyrate
CAS Number:15591-70-5
Molecular formula:C13H15NO2
Molecular Weight:217.26

67-56-1 Synthesis

67-56-1
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$9.00/25ml

133-32-4 Synthesis

133-32-4
637 suppliers
$10.00/5g

15591-70-5
18 suppliers
$105.00/50mg

Yield:15591-70-5 98%

Reaction Conditions:

with sulfuric acid at 20; for 5 h;

Steps:

53.a

) Methyl 4-(1 H-indol-3-yl)butanoateH₂SO₄ (3.5 ml_, 64.92 mmol) was added to a solution of indole-3-butyhc acid (4.0 g, 19.68 mmol) in MeOH (100 ml_). The reaction mixture was stirred at r.t. for 5 h, and poured into H₂O (150 ml_). It was extracted with CH₂CI₂ (2x100 ml_). The organic layer was dried over Na₂SO₄ (anhydrous), filtered and concentrated, to give 4.22 g of methyl 4-(1 H-indol-3-yl)butanoate (white solid, yield: 98%). The compound was submitted to next step without further purification. ¹H NMR (CDCI₃, 250 MHz) ppm: 7.97 (bs, 1 H), 7.61 (d, J = 7.7 Hz, 1 H), 7.35 (d, J = 8.0 Hz, 1 H), 7.24-7.07 (m, 2H), 7.23 (bs, 1 H), 3.66 (s, 3H), 2.81 (t, J = 7.4 Hz, 2H), 2.40 (t, J = 7.4 Hz, 2H), 2.06 (q, J = 7.4 Hz, 2H).

References:

WO2009/80722,2009,A2 Location in patent:Page/Page column 79-80