m,alpha-Dichlorotoluene → (3-Chloro-benzyl)-pyrrol-1-yl-carbamic acid tert-butyl ester

HRID 1511930Notes

Reaction equation

HRID 1511930 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Cl.[H-].[Na+]>>[C:1]([O:5][C:6](=[O:13])[N:7]([CH2:18][C:17]1[CH:20]=[CH:21][CH:22]=[C:15]([Cl:14])[CH:16]=1)[N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 12103m,alpha-DichlorotolueneHCID 24758Sodium hydrideHCID 49760548tert-Butyl 1H-pyrrol-1-ylcarbamate

Product 1

HCID 67230403(3-Chloro-benzyl)-pyrrol-1-yl-carbamic acid tert-butyl ester

Procedure

Prepared according to the benzylation condition used in Example 1 step b) from pyrrol-1-yl-carbamic acid tert-butyl ester (1.0 eq.), 3-chlorobenzyl chloride (1.03 eq.) and sodium hydride (1.3 eq.). ESI (m/z): 307 (M+H)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a3646afdb9f0423e8ae95ed60e0cd7c0
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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