1-Bromo-3-chloropropane → 5-(3-Chloro-propoxy)-2-(4,4-difluoro-piperidine-1-carbonyl)-pyrrolo[2,3-b]pyridine-1-carboxylic Acid tert-butyl Ester

HRID 1437700Notes

Reaction equation

HRID 1437700 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([OH:17])[CH:16]=[C:11]2[CH:10]=[C:9]1[C:18]([N:20]1[CH2:25][CH2:24][C:23]([F:27])([F:26])[CH2:22][CH2:21]1)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][CH2:36][CH2:37][Cl:38]>CC(=O)CC>[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([O:17][CH2:35][CH2:36][CH2:37][Cl:38])[CH:16]=[C:11]2[CH:10]=[C:9]1[C:18]([N:20]1[CH2:25][CH2:24][C:23]([F:27])([F:26])[CH2:22][CH2:21]1)=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 684239772-(4,4-Difluoro-piperidine-1-carbonyl)-5-hydroxy-pyrrolo[2,3-b]pyridine-1-carboxylic Acid tert-butyl Ester

Product 1

HCID 684252235-(3-Chloro-propoxy)-2-(4,4-difluoro-piperidine-1-carbonyl)-pyrrolo[2,3-b]pyridine-1-carboxylic Acid tert-butyl EsterYield 63%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The title compound was synthesized in analogy to example 1, intermediate a), from 2-(4,4-difluoro-piperidine-1-carbonyl)-5-hydroxy-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester, potassium carbonate and 1-bromo-3-chloropropane in 2-butanone to give the desired product as a colorless foam (63%).

Sources & evidence

ORD record
ord-6ffcffd3d9ce4eedacb7082a7fd1308f
Source dataset
uspto-grants-2009_11
Patent number
US07622466B2

Reaction notes

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