Carbon tetrabromide → HCID 86610733, compound

HRID 1784442Notes

Reaction equation

HRID 1784442 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@@H:9]([CH2:13][CH2:14]O)[NH:8][CH2:7][CH2:6]2.[F:16][C:17]([F:22])([F:21])[C:18]([NH2:20])=[O:19].C(Br)(Br)(Br)[Br:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@@H:9]([CH2:13][CH2:14][Br:24])[NH:8][CH2:7][CH2:6]2.[F:16][C:17]([F:22])([F:21])[C:18]([NH2:20])=[O:19]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86610732HCID 86610732, compound

Product 1

HCID 86610733HCID 86610733, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-methoxy-1-(R)-(2-hydroxyethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (330 mg, 1.09 mmol) obtained in step (b) of Example 190 and carbon tetrabromide (542 mg, 1.63 mmol) in dichloromethane (5 ml) was added gradually triphenyl phosphine (343 mg, 1.31 mmol) with stirring under cooling in a water bath. The resulting mixture was further stirred at room temperature, and after confirming the disappearance of the starting material by thin layer chromatography, the reaction mixture was evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (80:20) as the eluent to afford the title compound (390 mg, yield: 98%) as a colorless oil.

Workup

  1. temperatureunder cooling in a water bath
  2. stirringThe resulting mixture was further stirred at room temperature
  3. customthe reaction mixture was evaporated in vacuo
  4. customThe residue obtained
  5. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-04725603260849d48bb508a803e3335e
Source dataset
uspto-grants-2009_03
Patent number
US07504393B2

Reaction notes

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