Sodium Cyanide → HCID 21099504, compound

HRID 2376982Notes

Reaction equation

HRID 2376982 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[C-:27]#[N:28].[Na+]>CS(C)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([C:27]#[N:28])=[CH:22][CH:21]=2)(=[O:18])=[O:19])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 21099423HCID 21099423, compound

Product 1

HCID 21099504HCID 21099504, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

2,4-Difluoro-1-(2-{4-[(4-fluorophenyl)sulfonyl]phenyl}ethyl)benzene (Example 122, 20 mg, 0.053 mmol) was dissolved in dimethylsulfoxide (0.1 mL) and sodium cyanide (5.2 mg, 0.106 mmol) was added. The reaction was heated to 100° C. overnight. The cooled reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 25% ethyl acetate/isohexane, to yield the title compound as a white solid (7 mg, 36%) δH (400 MHz, d6 DMSO): 8.10-8.07 (4H, m), 7.89 (2H, d, J=8.4 Hz), 7.46 (2H, d, J=8.4 Hz), 7.29 (1H, q, J=7.6 Hz), 7.14-7.10 (1H, m), 6.98-6.94 (1H, m), 2.94-2.86 (4H, m).

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with 25% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-92552b70f0274145abb6d04dd33ab3af
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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