Boron tribromide → HCID 11530821, compound

HRID 2236085Notes

Reaction equation

HRID 2236085 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9]2[C:12]([C:26]#[N:27])=[C:13]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[CH:19]=3)=[O:17])[S:14][C:8]=2[CH2:7]1)=[O:5])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9]2[C:12]([C:26]#[N:27])=[C:13]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=3)=[O:17])[S:14][C:8]=2[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 4445478HCID 4445478, compound

Product 1

HCID 11530821HCID 11530821, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-cyano-2-{[1-(3-methoxy-phenyl)-methanoyl]-amino}-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid ethyl ester (0.16 mmol) is dissolved in 2.4 ml dichloromethane. 1.22 ml BBr3 (1M in dichloromethane) is added at −78° C. and the reaction mixture is stirred for 20 hours at room temperature. After aqueous workup and evaporation of the solvent, the curde product is recristallized from ethanol.

Workup

  1. customAfter aqueous workup and evaporation of the solvent

Sources & evidence

ORD record
ord-348b0dfb71f7416893bf7b29d857a7a8
Source dataset
uspto-grants-2010_05
Patent number
US07714134B2

Reaction notes

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