Methyl 5-chloro-4-nitrothiophene-2-carboxylate → Methyl 5-((3,5-difluoropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylate

HRID 1192263Notes

Reaction equation

HRID 1192263 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[S-:8].[Na+].Cl[C:12]1[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22]>>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[S:8][C:12]1[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22]

Participants

3

Reactant 2

HCID 13205564Methyl 5-chloro-4-nitrothiophene-2-carboxylateHCID 60207484Sodium 3,5-difluoropyridine-4-thiolate

Product 1

HCID 60207483Methyl 5-((3,5-difluoropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylateYield 67%

Procedure

Prepared according to the procedure described for example 18, sodium 3,5-difluoropyridine-4-thiolate (529 mg, 3.6 mmol) reacted with methyl 5-chloro-4-nitro-thiophene-2-carboxylate (800 mg, 3.6 mmol) to afford the titled product (800 mg, 67% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.91 (2H, s), 8.18 (1H, s), 3.85 (3H, s). MS m/z: 333.04 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-09c94e0177cc40c6a1278f4d58948c8b
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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