Bromine → 7-Bromo-2-(3-fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carboxylic acid methyl ester

HRID 1963096Notes

Reaction equation

HRID 1963096 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[CH3:28])=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[C:13]=1[CH:12]=[CH:11][CH:10]=[CH:9]2)=[O:4].[Br:29]Br.C1CCN2C(=NCCC2)CC1>C1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[CH3:28])=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[C:13]=1[CH:12]=[C:11]([Br:29])[CH:10]=[CH:9]2)=[O:4]

Participants

6

Reactant 3

HCID 24408BromineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 677721232-(3-Fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carboxylic acid methyl ester

Product 1

HCID 706641557-Bromo-2-(3-fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carboxylic acid methyl esterYield 69.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent

Procedure

The compound of example 11, step 3, (550 mg, 1.47 mmol) was dissolved in a mixture of benzene (15 ml) and chloroform (15 ml) and treated at room temperature with bromine (235 mg, 1.47 mmol) under stirring. After 2 h, DBU (224 mg, 1.47 mmol) was added and the mixture stirred for 18 h at room temperature. The solvent was removed in vacuo and the remaining residue was purified by silica gel chromatography (HEP/EA). 460 mg of the title compound were obtained.

Workup

  1. stirringthe mixture stirred for 18 h at room temperature
  2. customThe solvent was removed in vacuo
  3. customthe remaining residue was purified by silica gel chromatography (HEP/EA)

Sources & evidence

ORD record
ord-51b40a9912384f4d84ec98cf9c3a41ff
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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