benzyl N-(2-bromoethyl)carbamate → (2-Benzyloxycarbonylamino-ethyl)-[4-(2-chloro-phenyl)-pyridin-3-yl]-carbamic acid tert-butyl ester

HRID 878128Notes

Reaction equation

HRID 878128 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N:14]([CH:31]1[CH2:33]C1)[C:15](=[O:30])C1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1.[CH2:34]([O:41][C:42](=[O:47])[NH:43]CCBr)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CCCCCCC.C[O:56][C:57]([CH3:60])([CH3:59])[CH3:58]>>[C:57]([O:56][C:15](=[O:30])[N:14]([CH2:31][CH2:33][NH:43][C:42]([O:41][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:47])[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])([CH3:60])([CH3:59])[CH3:58]

Participants

4

Reactant 3

HCID 278694benzyl N-(2-bromoethyl)carbamateHCID 22389680MTBE heptaneHCID 86670746N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-N-cyclopropyl-3,5-bis-trifluoromethyl-benzamide2×

Product 1

HCID 70663219(2-Benzyloxycarbonylamino-ethyl)-[4-(2-chloro-phenyl)-pyridin-3-yl]-carbamic acid tert-butyl ester

Procedure

The title compound was prepared in analogy to example 85, intermediate c, from [4-(2-chloro-phenyl)-pyridin-3-yl]-carbamic acid tert-butyl ester (example 124, intermediate d) and (2-bromo-ethyl)-carbamic acid benzyl ester (CAS RN 53844-02-3) and using a gradient of n-heptane:tert-butyl methyl ether (100:0 to 30:70) for the chromatographic separation. Colorless foam (53%). MS (ESI): m/z=482.18 [M+H]+.

Workup

  1. customfor the chromatographic separation

Sources & evidence

ORD record
ord-713308de87fe41cfb7bdcaa921815af9
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…