Lithium Hydroxide → 3-Bromo-4-(4-trifluoromethyl-benzyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

HRID 1951644Notes

Reaction equation

C[O:2][C:3]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[C:8]2[C:21]([Br:24])=[CH:22][S:23][C:7]=2[CH:6]=1)=[O:4].[Li+].[OH-]>CO.C1COCC1>[Br:24][C:21]1[C:8]2[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:20])[F:19])=[CH:13][CH:12]=3)[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[S:23][CH:22]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of the crude product of Step 3 (4 g) in 50 ml of 1:1 MeOH/THF was added 25 ml of 1N aqueous LiOH solution. The reaction mixture was stirred at 55° C. for 4 h and the concentrated under reduced pressure to move the volatile solvent. The resulting aqueous solution was treated with 5 ml of AcOH and stirred for 2 h. The solid was collected by filtration to give 3.2 of the title compound as a white powder.

Workup

concentrationthe concentrated under reduced pressure
additionThe resulting aqueous solution was treated with 5 ml of AcOH
stirringstirred for 2 h
filtrationThe solid was collected by filtration

Sources & evidence

ORD record: ord-38c4d35a2e3347259536df4abfb41df9
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404736B2

Reaction notes

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