Phosphorus oxychloride → 7-(4-Chloropyrimidin-5-yl)-3-(4-fluorophenyl)isoxazolo[4,5-b]pyridine

HRID 871169Notes

Reaction equation

HRID 871169 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([C:17]4[C:18](O)=[N:19][CH:20]=[N:21][CH:22]=4)=[C:11]3[O:10][N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:18]1[C:17]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[N:9][O:10][C:11]=23)=[CH:22][N:21]=[CH:20][N:19]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518074HCID 178518074, compound

Product 1

HCID 867304227-(4-Chloropyrimidin-5-yl)-3-(4-fluorophenyl)isoxazolo[4,5-b]pyridineYield 100.6%

Conditions

Temperature
90 °C

Procedure

A suspension of 5-(3-(4-fluorophenyl)isoxazolo[4,5-b]pyridin-7-yl)pyrimidin-4-ol (45 mg, 0.146 mmol) in phosphorus oxychloride (503 μl, 5.40 mmol) was heated at 90° C. for 1 h, then allowed to cool to room temperature. The solvent was evaporated to afford the title compound (48 mg, 100%).

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7d72e5245b7f4fff9059a554ee95c29c
Source dataset
uspto-grants-2015_03
Patent number
US08969586B2

Reaction notes

Loading…