Dimethylformamide → HCID 66697817, compound

HRID 340602Notes

Reaction equation

HRID 340602 reaction equation
[C:1]([O:5][C:6](=[O:32])[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=2)(=[O:17])=[O:16])[N:12]([C:25]2[C:26]([F:31])=[N:27][CH:28]=[CH:29][CH:30]=2)[N:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:33][N:34](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:32])[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:33]#[N:34])[CH:19]=2)(=[O:17])=[O:16])[N:12]([C:25]2[C:26]([F:31])=[N:27][CH:28]=[CH:29][CH:30]=2)[N:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 66697793HCID 66697793, compound

Product 1

HCID 66697817HCID 66697817, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
110 °C

Procedure

A solution of tert-butyl({5-[(3-bromophenyl)sulfonyl]-1-(2-fluoropyridin-3-yl)-1H-pyrazol-3-yl}methyl)methylcarbamate (315 mg) and zinc cyanide (107 mg) in dimethylformamide (3 mL) was sufficiently deaerated, tetrakis(triphenylphosphine)palladium(0) (138 mg) was added, and the mixture was further deaerated. After stirring under an argon atmosphere at 110° C. for 2 hr, the reaction mixture was allowed to cool to room temperature, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1) to give the title compound as a yellow oil (yield 247 mg, yield 87%).

Workup

  1. temperatureto cool to room temperature
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1)

Sources & evidence

ORD record
ord-a0da2c85601c4e9ab47ac9fdd0642dac
Source dataset
uspto-grants-2014_11
Patent number
US08895588B2

Reaction notes

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