m-Chloroperbenzoic acid → 2-[[(4-Methoxy)pyridin-2-yl]methylsulfinyl]-6-fluoro-5-(imidazol-1-yl)-1H-benzimidazole

HRID 1004597Notes

Reaction equation

HRID 1004597 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][S:10][C:11]2[NH:15][C:14]3[CH:16]=[C:17]([F:25])[C:18]([N:20]4[CH:24]=[CH:23][N:22]=[CH:21]4)=[CH:19][C:13]=3[N:12]=2)[CH:4]=1.ClC1C=CC=C(C(OO)=[O:34])C=1.[K+].[Br-]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][S:10]([C:11]2[NH:15][C:14]3[CH:16]=[C:17]([F:25])[C:18]([N:20]4[CH:24]=[CH:23][N:22]=[CH:21]4)=[CH:19][C:13]=3[N:12]=2)=[O:34])[CH:4]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 253877Potassium BromideHCID 539610442-[[(4-Methoxy)pyridin-2-yl]methylthio]-6-fluoro-5-(imidazol-1-yl)-1H-benzimidazole

Product 1

HCID 538275152-[[(4-Methoxy)pyridin-2-yl]methylsulfinyl]-6-fluoro-5-(imidazol-1-yl)-1H-benzimidazoleYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound (0.32 g, 58%) was prepared by the above general procedure using 2-[[(4-methoxy)pyridin-2-yl]methylthio]-6-fluoro-5-(imidazol-1-yl)-1H-benzimidazole (0.53 g, 1.5 mmol) (obtained in example 5), m-chloroperbenzoic acid (50%, 0.62 g, 1.8 mmol) and dichloromethane (20 mL). IR (KBr) 3500, 1048 cm-1 ; 1H NMR (CD3OD) δ 3.86 (s, 3H, OCH3), 4.72 (ABq,J=10.8 Hz, Δv=15.6 Hz, 2H, SOCH2), 6.94 (m, 2H), 7.22 (s, 1H), 7.52 (s, 1H), 7.68 (d,J=10.8 Hz, 1H), 7.88 (d,J=7.6 Hz, 1H), 8.08 (s, 1H), 8.26 (d,J=5.6 Hz, 1H); Mass (m/z) 371 (M+.).

Sources & evidence

ORD record
ord-e0e57874b2ed499d8be0313042d4fc3b
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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