Ammonium formate → HCID 57562455, compound

HRID 1726062Notes

Reaction equation

HRID 1726062 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]CC3C=CC=CC=3)=[CH:14][CH:15]=2)[C:10]([C:25]2[N:26]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([O:34][CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)=[CH:29][CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:25]2[N:26]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([O:34][CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)=[CH:29][CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57562498HCID 57562498, compound

Product 1

HCID 57562455HCID 57562455, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 740 mg of 5-benzyloxy-3-[1-tert-butoxycarbonyl-5-(2-morpholin-4-ylethoxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester, of 328 mg of ammonium formate and of 234 mg of 10% palladium-on-charcoal in 56 ml of ethanol is heated at 70° C. for 35 minutes. The reaction mixture is then cooled to ambient temperature. The catalyst is filtered through paper and washed abundantly with ethanol to obtain 533 mg of the crude compound 3-[1-tert-butoxycarbonyl-5-(2-morpholin-4-ylethoxy)-1H-indol-2-yl]-5-hydroxyindazole-1-carboxylic acid tert-butyl ester.

Workup

  1. filtrationThe catalyst is filtered through paper
  2. washwashed abundantly with ethanol

Sources & evidence

ORD record
ord-a2a9744d497a4700a65286d7cfff0358
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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