Carbon tetrabromide → HCID 23019643, compound

HRID 1354197Notes

Reaction equation

HRID 1354197 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:7](=[O:23])[N:8]3[C:13]=2[C:12]([CH3:14])=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=2)[CH:10]=[CH:9]3)[CH2:3][CH2:2]1.C(Br)(Br)(Br)[Br:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:30][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:11]2[CH:10]=[CH:9][N:8]3[C:13]([C:12]=2[CH3:14])=[C:4]([CH:1]2[CH2:3][CH2:2]2)[CH:5]=[C:6]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:7]3=[O:23])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 23019641HCID 23019641, compound

Product 1

HCID 23019643HCID 23019643, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

327 mg of ethyl 1-cyclopropyl-8-(4-hydroxymethylphenyl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (Example 51) was dissolved in 11 ml of dichloromethane. 380 mg of carbon tetrabromide was added to the obtained solution, and they were cooled to 0° C. 355 mg of triphenylphosphine was added to the reaction mixture, and they were stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by the silica gel column chromatography (eluent: hexane/ethyl acetate=1/1) to obtain 291 mg of ethyl 8-(4-bromomethylphenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe obtained residue was purified by the silica gel column chromatography (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-f5f38ffec10e4d36a84ecac0ed5fdc3e
Source dataset
uspto-grants-2007_05
Patent number
US07223773B2

Reaction notes

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