Dimethylformamide → HCID 86691446, compound

HRID 540340Notes

Reaction equation

HRID 540340 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([N:12]2[CH2:18][CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[CH2:13]2)[CH:3]=1.[C:23]([O:27][C:28]([N:30]1[C@@H:34]([CH:35]=[CH2:36])[CH2:33][O:32][C:31]1([CH3:38])[CH3:37])=[O:29])([CH3:26])([CH3:25])[CH3:24].CN(C1CCCCC1)C1CCCCC1.CN(C)C=O>C(OCC)(=O)C.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:37][C:31]1([CH3:38])[N:30]([C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])[C@@H:34](/[CH:35]=[CH:36]/[C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([N:12]3[CH2:18][CH2:17][CH2:16][C:15]4[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=4[CH2:13]3)[CH:3]=2)[CH2:33][O:32]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24210N-Methyl dicyclohexylamineHCID 11020618tert-Butyl (4S)-4-ethenyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylateHCID 71255109HCID 71255109, compound

Product 1

HCID 86691446HCID 86691446, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 2-(4-chloroquinolin-2-yl)-2,3,4,5-tetrahydro-1H-2-benzazepine (310 mg, 1.0 mmol), (S)-2,2-dimethyl-4-vinyl-oxazolidine-3-carboxylic acid tert-butyl ester (273 mg, 1.2 mmol), bis(tri-tert-butylphosphine)palladium(0) (51 mg, 0.1 mmol), methyl dicyclohexylamine (293 mg, 1.5 mmol) and N,N-dimethylformamide (6 mL) was heated with stirring in a 20 mL microwave process vial for 2.5 hours at 120° C. under microwave irradiation. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate, and then concentrated under reduced pressure to give a residue which was purified by flash column to give 380 mg of product as a white solid (yield was 76%). MS obsd. (ESI+) [(M+H)+] 500.

Workup

  1. temperaturewas heated
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue which
  6. customwas purified by flash column

Sources & evidence

ORD record
ord-3d51165dfc094cdd9f3ac80b525936f0
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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