Sodium hydride → HCID 67301339, compound

HRID 1015359Notes

Reaction equation

HRID 1015359 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][OH:13])[CH2:8][CH2:7]1.[H-].[Na+].[F:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24](F)[C:21]=1[C:22]#[N:23]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][CH:6]1[CH2:7][CH2:8][CH:9]([CH2:12][O:13][C:24]2[CH:25]=[CH:26][CH:27]=[C:20]([F:19])[C:21]=2[C:22]#[N:23])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 746952,6-DifluorobenzonitrileHCID 67302146HCID 67302146, compound

Product 1

HCID 67301339HCID 67301339, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

[4-(3-Chlorobenzyl)cyclohexyl]-methanol (150 mg; 0.63 mmol) was added to a suspension of sodium hydride (33 mg; 0.82 mmol) in 3 mL of dimethylformamide at 0° C. After 2 hours, mixture was added to a mixture of 2,6-difluorobenzonitrile (88 mg; 0.63 mmol) in 2 mL of dimethylformamide at 0° C. After 16 hours mixture was quenched with 5 g of ice. Aqueous mixture was extracted with 5×15 mL of ethyl acetate. Combined ethyl acetates were washed with 6×15 mL water, brine and dried over MgSO4. Residue was purified via flash chromatography using 5-15% ethyl acetate in hexanes gradient to give 173 mgs of title compound. (77% yield).

Workup

  1. customAfter 16 hours mixture was quenched with 5 g of ice
  2. extractionAqueous mixture was extracted with 5×15 mL of ethyl acetate
  3. washCombined ethyl acetates were washed with 6×15 mL water, brine
  4. dry with materialdried over MgSO4
  5. customResidue was purified via flash chromatography

Sources & evidence

ORD record
ord-0b840fafcc1b4b7c8c5d24b180393dff
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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