HCID 86716211, compound → HCID 86716212, compound

HRID 512184Notes

Reaction equation

HRID 512184 reaction equation
[F:1][C:2]1([F:21])[CH2:7][CH2:6][C:5]([C:14]2[CH:15]=[N:16][C:17]([CH3:20])=[N:18][CH:19]=2)([C:8](N(OC)C)=[O:9])[CH2:4][CH2:3]1.[CH3:22][Mg+].[Br-]>C1COCC1>[F:21][C:2]1([F:1])[CH2:3][CH2:4][C:5]([C:8](=[O:9])[CH3:22])([C:14]2[CH:19]=[N:18][C:17]([CH3:20])=[N:16][CH:15]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 86716211HCID 86716211, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 86716212HCID 86716212, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,4-difluoro-N-methoxy-N-methyl-1-(2-methylpyrimidin-5-yl)cyclohexanecarboxamide (700 mg, 2.34 mmol) in THF (20 mL) was added MeMgBr (11.7 mL, 35.12 mmol, 3M in Et2O) at 0° C. and stirred at room temperature for 4 h. The reaction mixture was quenched by saturated NH4Cl at 0° C. and extracted with EtOAc (2×50 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated to give crude product, which was purified by flash chromatography (EtOAc: petroluem ether=1:3˜3:2) to give 1-(4,4-difluoro-1-(2-methylpyrimidin-5-yl)cyclohexyl)ethanone (350 mg, yield: 59%). 1H NMR (CDCl3 400 MHz): δ8.58 (s, 2H), 2.73 (s, 3H), 2.55-2.45 (m, 2H), 2.20-1.85 (m, 9H).

Workup

  1. customThe reaction mixture was quenched by saturated NH4Cl at 0° C.
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas purified by flash chromatography (EtOAc: petroluem ether=1:3˜3:2)

Sources & evidence

ORD record
ord-7da8b6c7b45748e4ac9db9ee8745a088
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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