HCID 21990990, compound → (2-Chloro-4-[1,3]oxazolo[4,5-b]pyridin-2-ylphenyl)acetonitrile

HRID 7740Notes

Reaction equation

HRID 7740 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[CH2:18][C:19]#[N:20])[C:5]([NH:7][C:8]1[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][N:9]=1)=O>O=P(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:14][C:13]3[C:8]([N:7]=2)=[N:9][CH:10]=[CH:11][CH:12]=3)[CH:15]=[CH:16][C:17]=1[CH2:18][C:19]#[N:20]

Participants

3

Reactant 1

HCID 21990990HCID 21990990, compound

Product 1

HCID 10171550(2-Chloro-4-[1,3]oxazolo[4,5-b]pyridin-2-ylphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

3-chloro-4-(cyanomethyl)-N-(3-hydroxypyridin-2-yl)benzamide (550 mg, 1.9 mmol) was refluxed in POCl3 (15 mL) for 2.5 h. Excess POCl3 was removed by distillation and the mixture was cooled to rt. The crude mixture was diluted with H2O. The aqueous layer was made basic (pH 14) with 1N NaOH and extracted with CH2Cl2 (3×20 mL). The residue was adsorbed onto silica gel and purified by automated flash chromatography using an EtOAc/hexane gradient to afford (2-chloro-4-[1,3]oxazolo[4,5-b]pyridin-2-ylphenyl)acetonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.65–8.63 (d, 1H), 8.41 (s, 1H), 8.30–8.27 (d, 1H), 7.93–7.90 (d, 2H), 7.77–7.74 (d, 2H), 7.38–7.34 (m, 2H) 3.95 (s, 2H). MS (ESI) 270 (M+H)+.

Workup

  1. customExcess POCl3 was removed by distillation
  2. additionThe crude mixture was diluted with H2O
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. custompurified by automated flash chromatography

Sources & evidence

ORD record
ord-c6164288fd3c4bcb8895ec6a0beca9ed
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Reaction notes

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