HCID 21099454, compound → HCID 21099518, compound

HRID 2376965Notes

Reaction equation

HRID 2376965 reaction equation
Br[C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])[CH:5]=[CH:4][C:3]=1[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19].[Cu][C:28]#[N:29]>CN(C)C=O.O>[F:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1/[CH:9]=[CH:8]/[C:6]1[CH:5]=[CH:4][C:3]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[C:2]([CH:7]=1)[C:28]#[N:29]

Participants

5

Reactant 2

HCID 21099454HCID 21099454, compoundHCID 178418546HCID 178418546, compound2×

Product 1

HCID 21099518HCID 21099518, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

2-Bromo-4-[(E)-2-(2,4-difluorophenyl)vinyl]-1-(phenylsulfonyl)benzene (Example 55, 130 mg, 0.3 mmol) and copper(I) cyanide (40 mg, 0.45 mmol) were combined in N,N-dimethylformamide (20 mL) and heated to 130° C. for 3 hours. Further copper(I) cyanide (40 mg, 0.45 mmol) was added and heating continued overnight. The cooled reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water (×3) and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 20-30% ethyl acetate/isohexane, followed by trituration with diethyl ether to give the title compound (50 mg, 44%). δH (360 MHz, d6 DMSO): 8.41 (1H, d, J=1.6 Hz), 8.28 (1H, d, J=8.4 Hz), 8.14 (1H, dd, J=1.7, 8.4 Hz), 8.01-7.98 (2H, m), 7.86-7.64 (4H, m), 7.58 (1H, d, J=16.6 Hz), 7.37 (1H, d, J=16.8 Hz), 7.32-7.28 (1H, m), 7.17 (1H, td, J=2.4, 8.5 Hz).

Workup

  1. temperatureheating continued overnight
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water (×3) and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography on silica
  8. washeluting with 20-30% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-09ba8ac56bbf4f4a979c60d011592a8f
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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