1-BENZYL-4-HYDROXY-5-AZAINDOLE synthesis

4synthesis methods

Product Name:1-BENZYL-4-HYDROXY-5-AZAINDOLE
CAS Number:26956-47-8
Molecular formula:C14H12N2O
Molecular Weight:224.26

2-Propenoyl azide, 3-[1-(phenylmethyl)-1H-pyrrol-2-yl]-, (2E)-

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26956-47-8
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Yield:26956-47-8 81%

Reaction Conditions:

with tributyl-amine in diphenylether;4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 195; for 1 h;

Steps:

INTERMEDIATE 89 [1-BENZYL-1,] 5-dihydro-pyrrolo [3, 2-c] pyridin-4-one

INTERMEDIATE 89 [1-BENZYL-1,] 5-dihydro-pyrrolo [3, 2-c] pyridin-4-one was prepared by the literature procedure according to C. Ducrocq; E. Bisangi; J-M, Lhoste; J. Mispelter; Tetrahedron, Vol 32, pp 773-780, (1976). To a stirred solution [OF N-TRIBUTYLAMINE] (30 mL) in diphenyl ether (150 mL) heated to 195 [°C] was slowly added during 30 minutes a solution of the acyl azide dissolved in DCM (150 mL). The reaction mixture was stirred at [195 °C] for 1 hour and then cooled to room temperature. Pentane (1.0 L) and ether (1.0 L) was added to the reaction mixture and the precipitate was collected by filtration. The crude solid was triturated with ether to give 6.89 g [(81 %)] of the pure product. Purity HPLC >95%; MS [(ESI)] m/z 225 (m+H) [; 1H] NMR (DMSO-d6, [25 °C,] 270.16) 8 10.84 (br s, 1 H), 7.43-7. 14 (m, 6 H), 7.00 (d, J = 7.12 Hz, 1 H), 6.57-6. 49 (m, 2 H), 5.83 (s, 2 H).

References:

WO2004/828,2003,A1

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60290-03-1
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References

60290-03-1
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26956-47-8
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References

1-(PHENYLMETHYL)-1H-PYRROLE-2-CARBOXALDEHYDE

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26956-47-8
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References