HCID 89704811, compound → HCID 89704879, compound

HRID 929050Notes

Reaction equation

HRID 929050 reaction equation
[N:1]([C:4]1[C:13]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])[C:5]=1[F:30])=[N+]=[N-].[H][H]>CO.[Pd]>[NH2:1][C:4]1[C:13]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])[C:5]=1[F:30]

Participants

5

Reactant 2

HCID 89704811HCID 89704811, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 89704879HCID 89704879, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 4-azido-5-(benzylthio)-3-fluoro-2-((2-fluorophenyl)amino)benzoate (10.38 g, 24.36 mmol) in MeOH (100 mL) was added and 10% palladium on carbon (1.55 g) under nitrogen atmosphere. Then the nitrogen atmosphere was completely changed to hydrogen atmosphere. The mixture was stirred for 6 h at ambient temperature. After the insoluble matter was filtered off, the solvent was evaporated in vacuo to give the desired product (9.79 g, 100% yield). 1H NMR (400 MHz, CDCl3) δ 8.98 (s, 1H), 7.69 (s, 1H), 7.19-7.17 (m, 3H), 7.15-6.83 (m, 6H), 4.54 (s, 2H), 3.79 (s, 2H), 3.75 (s, 3H).

Workup

  1. filtrationAfter the insoluble matter was filtered off
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-d56b4b391b5f4cfdbdee9c77976c4cc4
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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