tert-Butyl 3-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxamido)pyrrolidine-1-carboxylate → tert-Butyl 3-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridine-2-carboxamido)pyrrolidine-1-carboxylate

HRID 500910Notes

Reaction equation

HRID 500910 reaction equation
[F:1][C:2]1[CH:32]=[C:31]([N+:33]([O-])=O)[CH:30]=[CH:29][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]([NH:16][CH:17]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]3)=[O:15])[S:13][C:6]=12>CO.[OH-].[OH-].[Pd+2]>[NH2:33][C:31]1[CH:30]=[CH:29][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]([NH:16][CH:17]4[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[CH2:18]4)=[O:15])[S:13][C:6]=23)=[C:2]([F:1])[CH:32]=1

Participants

4

Reactant 1

HCID 59424637tert-Butyl 3-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxamido)pyrrolidine-1-carboxylate

Product 1

HCID 59424462tert-Butyl 3-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridine-2-carboxamido)pyrrolidine-1-carboxylateYield 70.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 289 (90 mg, 0.18 mmol) and Pd(OH)2 in MeOH (2 mL) was hydrogenated at 1 atm for 1 h. The catalyst was filtered off and the filtrate was concentrated to afford the title compound 290 (60 mg, 70% yield) as a yellowish solid. MS (m/z): 473.2 (M+H) (found).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-57b46d9dd2844545929781a8f62a467c
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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