Tert-butyl 4-{2-[(4-bromophenyl)amino]-1-methylbenzimidazol-5-yloxy}pyridine-2-carboxylate → 4-{2-[(4-Bromophenyl)amino]-1-methylbenzimidazol-5-yloxy}pyridine-2-carboxylic acid

HRID 13449

Reaction equation

HRID 13449 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH3:14])[C:12]3[CH:15]=[CH:16][C:17]([O:19][C:20]4[CH:25]=[CH:24][N:23]=[C:22]([C:26]([O:28]C(C)(C)C)=[O:27])[CH:21]=4)=[CH:18][C:11]=3[N:10]=2)=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH3:14])[C:12]3[CH:15]=[CH:16][C:17]([O:19][C:20]4[CH:25]=[CH:24][N:23]=[C:22]([C:26]([OH:28])=[O:27])[CH:21]=4)=[CH:18][C:11]=3[N:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 22041284Tert-butyl 4-{2-[(4-bromophenyl)amino]-1-methylbenzimidazol-5-yloxy}pyridine-2-carboxylate

Product 1

HCID 220406464-{2-[(4-Bromophenyl)amino]-1-methylbenzimidazol-5-yloxy}pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the product of step 7 in trifluoroacetic acid was treated with two drops of water at room temperature for 3-4 hours or until the reaction was determined to be complete by HPLC. The reaction was evaporated under reduced pressure to afford the product as a red-orange oil in quantitative yield. MS: MH+=439.

Workup

  1. customThe reaction was evaporated under reduced pressure

Sources & evidence

ORD record
ord-33af28af016b497fa6bf2bf439a5eae2
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Linked notes

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