HCID 70663318, compound → HCID 136414058, compound

HRID 878302Notes

Reaction equation

HRID 878302 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[N:21]([CH3:38])[C:22](=[O:37])[C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:24]=1)C1C=CC=CC=1>CO.CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[N:21]([CH3:38])[C:22](=[O:37])[C:23]1[CH:28]=[C:27]([C:29]([F:31])([F:32])[F:30])[CH:26]=[C:25]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:24]=1

Participants

5

Reactant 1

HCID 70663318HCID 70663318, compound

Product 1

HCID 136414058HCID 136414058, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[4-(2-benzyloxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide (200 mg, 370 μmol, example 258) in MeOH (2 mL) and EtOAc (2.00 mL) was added 10% palladium on charcoal (30 mg, 370 μmol) under argon atmosphere. The reaction was evacuated and purged with hydrogen gas. The reaction was stirred for 5 hours at 1.7 bar under H2 atmosphere. The reaction mixture was filtered over dicalite and the filtrate was concentrated under vacuum. The residue was purified by silica gel chromatography on a 20 g column using an MPLC (Flashmaster) system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless foam (150 mg, 90%). MS (ESI): m/z=451.094 [M+H]+.

Workup

  1. customThe reaction was evacuated
  2. custompurged with hydrogen gas
  3. filtrationThe reaction mixture was filtered over dicalite
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe residue was purified by silica gel chromatography on a 20 g column
  6. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-2681632c23a94ba292f611cdd1e51091
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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