HCID 67980820, compound → HCID 67981016, compound

HRID 1427436Notes

Reaction equation

HRID 1427436 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[N:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:18]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH:29]1([Mg]Br)[CH2:31][CH2:30]1>O1CCCC1>[CH:29]1([N:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:27])[F:28])=[CH:8][CH:7]=3)=[CH:10][CH:11]=2)[C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:18]=2)[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 67980820HCID 67980820, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 67981016HCID 67981016, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of methyl 6-((4′-(trifluoromethyl)biphenyl-4-yl)methyleneamino)nicotinate (600 mg, 1.56 mmol) in tetrahydrofuran (10 mL) was added cyclopropylmagnesium bromide (5 mL, 2N in THF, 8 mmol). The reaction was stirred at 0° C. for 1 hr, then warmed to room temperature and left stirring for 12 h. The reaction was quenched with saturated ammonium chloride and extracted with ethyl acetate (3×15 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. Purification by preparative TLC (5:1 petroleum ether:ethyl acetate) gave methyl 6-(cyclopropyl(4′-(trifluoromethyl)biphenyl-4-yl)methylamino)nicotinate (130 mg).

Workup

  1. temperaturewarmed to room temperature
  2. waitleft
  3. stirringstirring for 12 h
  4. customThe reaction was quenched with saturated ammonium chloride
  5. extractionextracted with ethyl acetate (3×15 mL)
  6. dry with materialThe combined organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by preparative TLC (5:1 petroleum ether:ethyl acetate)

Sources & evidence

ORD record
ord-573a173c34bb473b9cc1a4a798d9189d
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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