1-Bromo-3-chloro-5-cyclopropylbenzene → (4-Tert-butylbenzyl)-[2-(3-chloro-5-cyclopropylphenyl)-ethyl]-amine

HRID 19790Notes

Reaction equation

HRID 19790 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[CH:5]=[C:4]([Cl:11])[CH:3]=1.[C:12]([C:16]1[CH:29]=[CH:28][C:19]([CH2:20][N:21]2[CH2:25][CH2:24]OS2(=O)=O)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]>>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([CH2:20][NH:21][CH2:25][CH2:24][C:2]2[CH:7]=[C:6]([CH:8]3[CH2:10][CH2:9]3)[CH:5]=[C:4]([Cl:11])[CH:3]=2)=[CH:28][CH:29]=1)([CH3:14])([CH3:13])[CH3:15]

Participants

3

Reactant 2

HCID 665209601-Bromo-3-chloro-5-cyclopropylbenzeneHCID 866139913-(4-Tert-butylbenzyl)-[1,2,3]oxathiazolidine 2,2-dioxide

Product 1

HCID 68562711(4-Tert-butylbenzyl)-[2-(3-chloro-5-cyclopropylphenyl)-ethyl]-amineYield 63.8%

Procedure

The title compound was synthesized in analogy to example S6-C using 1-bromo-3-chloro-5-cyclopropylbenzene (96 mg, 0.71 mmol) and 3-(4-tert-butylbenzyl)-[1,2,3]oxathiazolidine 2,2-dioxide (36 mg, 0.89 mmol). The residue was purified by flash column chromatography to give the desired product (155 mg, 39%) as a colorless oil. MS (ISP) 342.2 (M+H)+.

Workup

  1. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-425dc250e5a54e08a1319a363034105e
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Reaction notes

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