HCID 23614737, compound → HCID 10406948, compound

HRID 1768464Notes

Reaction equation

HRID 1768464 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C:11]([CH:25]=[O:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1.[CH3:27][Mg]Br>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C:11]([CH:25]([OH:26])[CH3:27])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 23614737HCID 23614737, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 10406948HCID 10406948, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 75 mg (0.21 mmol) of aldehyde 3-1 in THF at −78° C. was added 80 μL (0.25 mmol) of methyl magnesium bromide solution (3M in Et2O). After stirring 1 h at that temperature, an additional 80 μL of the Grignard reagent was added and stirring was continued for 1 h more. The reaction was quenched with saturated NH4Cl, partitioned between brine and EtOAc, the organic phase washed with brine, dried over MgSO4, and concentrated. The residue was purified by column chromatography on silica gel with EtOAc/hexanes to provide 5-1 as a white solid. Data for 5-1: 1HNMR (500 MHz, CDCl3) δ 7.6 (m, 2H), 7.4-7.2 (m, 3H), 7.1-6.9 (m, 3H), 6.5 (s, 1H), 5.05 (m, 1H), 4.8 (m, 1H), 4.6 (m, 1H), 4.35 (m, 1H), 2.8 (s, 6H), 1.4 (m, 3H) ppm. HRMS (ES) calc'd M+H for C21H22F2N2O2: 373.1722. Found: 373.1713.

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. customThe reaction was quenched with saturated NH4Cl
  4. custompartitioned between brine and EtOAc
  5. washthe organic phase washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel with EtOAc/hexanes

Sources & evidence

ORD record
ord-35c7891300c64750b5791d19ef4bc0fd
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

Loading…