tert-Butyl piperazine-1-carboxylate → HCID 86630401, compound

HRID 1710609Notes

Reaction equation

HRID 1710609 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][CH:12]([F:14])[F:13].C([O:19][C:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21])(C)(C)C.[F:28][CH:29]([F:41])[O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[S:37](Cl)(=[O:39])=[O:38]>>[F:28][C:12]([F:13])([F:14])[C:20]([OH:19])=[O:21].[F:41][CH:29]([F:28])[O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[S:37]([NH:8][C:6]1[CH:5]=[CH:4][C:3]([O:11][CH:12]([F:14])[F:13])=[C:2]([N:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]2)[CH:7]=1)(=[O:39])=[O:38]

Participants

4

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 133147042-Bromo-1-(difluoromethoxy)-4-nitrobenzene2×HCID 137294512-(Difluoromethoxy)benzene-1-sulfonyl chloride

Product 1

HCID 86630401HCID 86630401, compound

Procedure

The compound was prepared starting from commercially available 2-bromo-4-nitrophenol, which was reacted with 2-chloro-2,2-difluoroacetophenone (J. Hu et al., J. Org. Chem., 2006, 71, 9845) to yield 2-bromo-1-difluoromethoxy-4-nitro-benzene. Subsequent Buchwald-Hartwig coupling of 2-bromo-1-difluoromethoxy-4-nitro-benzene with tert.butyloxycarbonyl-piperazine by analogy to preparation example 3.1, reduction of the nitro group to the corresponding aniline by analogy to preparation example 3.2, subsequent coupling with commercially available 2-difluoromethoxybenzene-sulfonylchloride by analogy to preparation example 1.4, and final deprotection under acidic conditions by analogy to example 1 yielded the title compound.

Workup

  1. customto preparation example 1.4

Sources & evidence

ORD record
ord-04424bbd0bed4d449e3216103d9fdcdb
Source dataset
uspto-grants-2010_09
Patent number
US07790727B2

Reaction notes

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