Azanium;hydrate → 2-(1H-indol-2-yl)benzo[d]oxazole-7-carboxamide

HRID 415233Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[O:11][C:12]2[C:18]([C:19]([O:21]C)=O)=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1.O.[NH4+:24]>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[O:11][C:12]2[C:18]([C:19]([NH2:24])=[O:21])=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1

Participants

Reactant 2

HCID 22024077Azanium;hydrate

HCID 66621353methyl 2-(1H-indol-2-yl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 666210082-(1H-indol-2-yl)benzo[d]oxazole-7-carboxamideYield 51%

Procedure

Methyl 2-(1H-indol-2-yl)benzo[d]oxazole-7-carboxylate (70 mg, 0.24 mmol) in ammonium water (10 mL) was stirred at 35° C. overnight. Then the suspension was filtered, and the solid was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 1:1) to obtain 2-(1H-indol-2-yl)benzo[d]oxazole-7-carboxamide as a solid (32 mg, yield 51%). 1H-NMR (400 MHz, DMSO-d6) δ 6.54 (s, 1H), 7.11-7.13 (t, J=8 Hz, 1H), 7.26-7.30 (t, J=8 Hz, 1H), 7.48-7.54 (dd, J1=16 Hz, J2=8 Hz, 2H), 7.70-7.72 (d, J=8 Hz, 1H), 7.84-7.86 (d, 1H), 7.88 (brs, 1H), 7.93-7.95 (d, J=8 Hz, 1H), 8.01 (brs, 1H), 12.47 (brs, 1H); LC-MS (ESI) m/z 278 [M+1]+.

Workup

filtrationThen the suspension was filtered
customthe solid was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 1:1)

Sources & evidence

ORD record: ord-89c3bda2a5ba4dc6a175e3b5d6ad421e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088760B2

Reaction notes

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