Pyridine → HCID 70816351, compound

HRID 1843026Notes

Reaction equation

HRID 1843026 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:23]([CH3:37])[C:24]([NH:26][CH2:27][C:28]2[NH:32][N:31]=[C:30]([C:33]([F:36])([F:35])[F:34])[CH:29]=2)=[O:25])[CH:15]=[CH:16][C:17]=1[CH2:18][S:19]([CH3:22])(=[O:21])=[O:20].N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(Cl)Cl>[F:11][C:12]1[CH:13]=[C:14]([CH:23]([CH3:37])[C:24]([NH:26][CH2:27][C:28]2[N:32]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[N:31]=[C:30]([C:33]([F:36])([F:34])[F:35])[CH:29]=2)=[O:25])[CH:15]=[CH:16][C:17]=1[CH2:18][S:19]([CH3:22])(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 1049PyridineHCID 2856454-Fluorophenylboronic acidHCID 70816627HCID 70816627, compound

Product 1

HCID 70816351HCID 70816351, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Fluorophenylboronic acid (41 mg, 0.295 mmol), 2-(3-fluoro-4-(methylsulfonylmethyl)phenyl)-N-((3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)propanamide (60 mg, 0.147 mmol) and copper(II)-acetate (0.021 mL, 0.221 mmol) were added to DCM (2.2 mL). At room temperature was added pyridine (0.238 mL, 2.946 mmol) and the mixture was stirred for overnight. The reaction mixture was concentrated in vacuo, the solid obtained was purified by CC (eluent: cyclohexane/ethyl acetate (1:2)) to afford 2-[3-fluoro-4-(methylsulfonyl-methyl)-phenyl]-N-[[2-(4-fluorophenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]-propionamide (55 mg, 75%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe solid obtained
  3. customwas purified by CC (eluent: cyclohexane/ethyl acetate (1:2))

Sources & evidence

ORD record
ord-eaad41707af34d8fa41296ec41d254bd
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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