Acetamide → 4-(5-Acetylamino-3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid benzyl ester

HRID 730838Notes

Reaction equation

HRID 730838 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][C:20](Br)=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([NH2:31])(=[O:30])[CH3:29].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][C:20]([NH:31][C:28](=[O:30])[CH3:29])=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 178AcetamideHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 674006394-(5-Bromo-3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 674009404-(5-Acetylamino-3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(5-bromo-3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid benzyl ester from step (a) above (300 mg, 0.677 mmol), acetamide (60 mg, 1 mmol, Aldrich), tris (dibenzylideneacetone) dipalladium (0) chloroform adduct (70 mg, 0.068 mmol, Strem Chemicals), 4,5-bis (diphenylphosphino)-9,9-dimethylxanthene (78 mg, 0.135 mmol, Aldrich) and cesium carbonate (331 mg, 1.01 mmol, Aldrich) in 1,4-dioxane (4 mL) was subjected to microwave irradiation at 170° C. for 0.5 h. The mixture was cooled to room temperature and was filtered. The filtrate was purified by silica gel column chromatography (2%-100% EtOAc/hexane) to give the title compound as a light-brown solid. MS (ESI, positive ion) m/z: 423 (M+1).

Workup

  1. customirradiation at 170° C. for 0.5 h
  2. filtrationwas filtered
  3. customThe filtrate was purified by silica gel column chromatography (2%-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-d5be3002e82e41ae90f75cef39ecbacb
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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