m-Chloroperbenzoic acid → HCID 18446603, compound

HRID 1269051Notes

Reaction equation

HRID 1269051 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([S:23][CH3:24])[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:4][N:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:30]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([S:23]([CH3:24])=[O:30])[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18446588HCID 18446588, compound

Product 1

HCID 18446603HCID 18446603, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold (0° C.) solution of 2-(2-fluoro-4-pyridinyl)-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridine (1.81 g, 5.36 mmol) in dichloromethane (100 mL) was added 3-chloroperoxybenzoic acid (1.39 g, 70%, 5.63 mmol). The reaction mixture was warmed to room temperature and stirred 16 hours. The reaction mixture was diluted with 100 mL dichloromethane and washed with saturated aqueous sodium bicarbonate solution. The organic layer was concentrated in vacuo to give 1.84 g of 2-(2-fluoro-4-pyridinyl)-3-[2-(methylsulfinyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridine of 90% purity as a greenish grey solid. This material was carried on without further purification. 1H NMR (DMSO-d6) δ 8.92 (d, 1H), 8.75 (d, 1H), 8.54 (d, 1H), 8.38 (d, 1H), 7.63–7.59 (m, 2H), 7.48 (s, 1H), 7.32 (d, 1H), 7.24 (t, 1H), 2.87 (s, 3H); 19F NMR (DMSO-d6) δ −68.05; MS m/z 354 (M+1).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-2506f7b586a74de2a6826bc672a84465
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

Loading…