HCID 59556324, compound → HCID 59556307, compound

HRID 1172691Notes

Reaction equation

HRID 1172691 reaction equation
[F:1][C:2]1[CH:9]=[C:8](/[CH:10]=[C:11](/[C:16]2[S:20][C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[N:18][C:17]=2[CH3:31])\[CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]>CO.C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:9]=[C:8]([CH2:10][CH:11]([C:16]2[S:20][C:19]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:26]=3)=[N:18][C:17]=2[CH3:31])[CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 1

HCID 59556324HCID 59556324, compound

Product 1

HCID 59556307HCID 59556307, compoundYield 74.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.6 g 2-Fluoro-4-{(E)-2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-hex-1-enyl}-benzonitrile were dissolved in a mixture of 10 ml methanol and 10 ml ethyl acetate. 300 mg palladium (5% on charcoal) were added and the mixture stirred at room temperature under a hydrogen atmosphere. After three hours the catalyst was filtered off through a pad of celite and the filtrate evaporated in vacuo. The residue was purified by reversed phase HPLC to obtain 1.2 g 2-Fluoro-4-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-hexyl}-benzonitrile as a lyophilisate. C24H22F4N2S (446.51), MS (ESI): 447.2 (M+H+).

Workup

  1. filtrationAfter three hours the catalyst was filtered off through a pad of celite
  2. customthe filtrate evaporated in vacuo
  3. customThe residue was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-81ce2901d5b04444b9a670558ee6e886
Source dataset
uspto-grants-2010_11
Patent number
US07834030B2

Reaction notes

Loading…