HCID 59774917, compound → HCID 25057140, compound

HRID 2422503Notes

Reaction equation

HRID 2422503 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][N:19]4[CH:23]=[C:22]([C:24]([OH:32])([C:28]([F:31])([F:30])[F:29])[CH2:25][CH:26]=[CH2:27])[N:21]=[N:20]4)=[CH:15][CH:16]=3)[O:11][C:10](=[O:33])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][N:19]4[CH:23]=[C:22]([C:24]([OH:32])([C:28]([F:30])([F:31])[F:29])[CH2:25][CH2:26][CH3:27])[N:21]=[N:20]4)=[CH:15][CH:16]=3)[O:11][C:10](=[O:33])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 59774917HCID 59774917, compound

Product 1

HCID 25057140HCID 25057140, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(3-fluorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)but-3-en-1-yl]-1H-1,2,3-triazol-1-yl}methyl)-2H-chromen-2-one from Step 5 (56 mg, 0.122 mmol) in EtOAc (2 mL) was stirred under H2 (1 atm), in the presence of 10% Pd/C (12 mg), for 17 h. After H2 was evacuated and the system purged with nitrogen, the reaction mixture was filtered through celite. The cake was rinsed with EtOAc and the filtrate concentrated. The residue was subjected to chromatography on silica gel (EtOAc/toluene 25:75) affording the title compound (50 mg). MS (−ESI): 460 (M−H)−.

Workup

  1. customAfter H2 was evacuated
  2. customthe system purged with nitrogen
  3. filtrationthe reaction mixture was filtered through celite
  4. washThe cake was rinsed with EtOAc
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-0ccfa7427dc94cd9a5099c1b6adef5df
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

Loading…