Ammonia → 2-(2-Fluoro-4-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide

HRID 415345Notes

Reaction equation

HRID 415345 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[O:15][C:16]2[C:22]([C:23](OC)=[O:24])=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.[NH3:27]>CO>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[O:15][C:16]2[C:22]([C:23]([NH2:27])=[O:24])=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66620942Methyl 2-(2-fluoro-4-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 441816742-(2-Fluoro-4-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxamideYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(2-fluoro-4-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxylate (500 mg, 1.43 mmol) was added to ammonia in methanol (30 mL) and the mixture was stirred at room temperature for 3 days. Then the solid was filtered, washed with methanol and dried in vacuum to obtain 2-(2-fluoro-4-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide as white solid (300 mg, yield 62%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 7.52-7.56 (t, J=7.6 Hz, 1H), 7.85-7.89 (m, 5H), 7.95-7.97 (d, J=8.4 Hz, 1H), 8.03-8.05 (m, 2H), 8.45-8.49 (t, J=7.6 Hz, 1H); 8.72-8.73 (d, J=4.4 Hz, 2H); LC-MS (ESI) m/z: 334 (M+1)+.

Workup

  1. filtrationThen the solid was filtered
  2. washwashed with methanol
  3. customdried in vacuum

Sources & evidence

ORD record
ord-2d0d7543c50445148607bc7d9764c50f
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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