m-Chloroperbenzoic acid → 2-(Chloromethyl)-3,4-dimethoxypyridine

HRID 2363797Notes

Reaction equation

HRID 2363797 reaction equation
[Cl:1][CH2:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][N:4]=1.[SH:13][C:14]1[NH:15][C:16]2[CH:22]=[C:21]([O:23][CH:24]([F:26])[F:25])[CH:20]=[CH:19][C:17]=2[N:18]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>>[CH3:12][O:11][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][S+:13]([O-:35])[C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([O:23][CH:24]([F:25])[F:26])=[CH:22][C:16]=3[N:15]=2)[C:8]=1[O:9][CH3:10].[Cl:1][CH2:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 50797222-(Chloromethyl)-3,4-dimethoxypyridineHCID 178506404HCID 178506404, compound

Product 2

HCID 50797222-(Chloromethyl)-3,4-dimethoxypyridineHCID 178493214Pantoprazole

Procedure

In one of the processes described in this patent application, 2-chloromethyl-3,4-dimethoxy pyridine was reacted with 2-mercapto-5-difluoromethoxy benzimidazole to prepare a precursor sulfide, which was isolated and oxidized by using metachloroperbenzoic acid to yield pantoprazole base in a yield of 102% by weight with respect to 2-chloromethyl-3,4 dimethoxy pyridine.

Workup

  1. customwhich was isolated

Sources & evidence

ORD record
ord-ddbfc449942a4bb4a6d4634d47f5dbd1
Source dataset
uspto-grants-2014_04
Patent number
US08691995B2

Reaction notes

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