3-[4-fluoro-3-(2-hydroxy-ethoxy)-phenyl]-1-trityl-5-nitro-1H-indazole → 3-[4-fluoro-3-(2-hydroxy-ethoxy)-phenyl]-1-trityl-1H-indazol-5-ylamine

HRID 1038141Notes

Reaction equation

HRID 1038141 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=3)[N:10]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:9]=2)=[CH:4][C:3]=1[O:39][CH2:40][CH2:41][OH:42]>CO.C1(C)C=CC=CC=1.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[N:10]([C:20]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:9]=2)=[CH:4][C:3]=1[O:39][CH2:40][CH2:41][OH:42]

Participants

4

Reactant 1

HCID 689614523-[4-fluoro-3-(2-hydroxy-ethoxy)-phenyl]-1-trityl-5-nitro-1H-indazole

Product 1

HCID 685307603-[4-fluoro-3-(2-hydroxy-ethoxy)-phenyl]-1-trityl-1H-indazol-5-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21867641Toluene methanolSolvent

Procedure

A suspension of 3-[4-fluoro-3-(2-hydroxy-ethoxy)-phenyl]-1-trityl-5-nitro-1H-indazole 14AX (1.5 g) and catalytic amount of Pd on carbon (5 wt %, 300 mg) in 40 mL of methanol/toluene (1:1) was stirred under a hydrogen atmosphere for 1 d and filtered through Celite. The filtrate was concentrated to provide 3-[4-fluoro-3-(2-hydroxy-ethoxy)-phenyl]-1-trityl-1H-indazol-5-ylamine 15AX (1.4 g) as an off-white solid.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b7bf2f684a9749849c22232992aaec69
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

Loading…