Pentafluorophenol → HCID 58989934, compound

HRID 1663087Notes

Reaction equation

HRID 1663087 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=[O:12])=[CH:3][CH:2]=1.[F:18][C:19]1[C:24]([F:25])=[C:23]([F:26])[C:22]([F:27])=[C:21]([F:28])[C:20]=1O>CCOC(C)=O>[F:18][C:19]1[C:20]([O:12][C:11](=[O:13])[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[NH:8][CH2:7][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[C:21]([F:28])[C:22]([F:27])=[C:23]([F:26])[C:24]=1[F:25]

Participants

4

Reactant 2

HCID 13041PentafluorophenolHCID 3239010HCID 3239010, compound

Product 1

HCID 58989934HCID 58989934, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 2-[(Pyridin-4-ylmethyl)-amino]-benzoic acid (preparation 1, 300 mg) in EtOAC (10 ml) was added 2,3,4,5,6-pentafluorophenol (413 mg) followed by drop-wise addition of a solution of N,N-dicyclohexyl-carbodiimide (461 mg) in EtOAc (5 ml). The reaction mixture was stirred at room temperature for 15 hours. The formed precipitate was removed by filtration and the filtrate was evaporated under reduced pressure. The remaining material was subjected to column chromatography on silica gel (petroleum ether/EtOAc as eluent) and gave the title compound (352 mg). 13C-NMR (DMSO-d6) δ 163.2, 151.4, 149.7, 148.1, 140.9, 138.9, 137.6, 136.9, 131.9, 124.7, 121.9, 115.6, 112.5, 105.5, 44.7.

Workup

  1. customThe formed precipitate was removed by filtration
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0fb3e5dfae3241b99173ac98e7eddf38
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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