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

HRID 1038139Notes

Reaction equation

HRID 1038139 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([N+:22]([O-])=O)[CH:20]=3)[N:15]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH3:12]>CO.C1(C)C=CC=CC=1.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH2:22])[CH:20]=3)[N:15]([C:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH3:12]

Participants

4

Reactant 1

HCID 689643703-[3-fluoro-4-(2-methoxy-ethoxy)-phenyl]-1-trityl-5-nitro-1H-indazole

Product 1

HCID 685308443-[3-fluoro-4-(2-methoxy-ethoxy)-phenyl]-1-trityl-1H-indazol-5-ylamineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21867641Toluene methanolSolvent

Procedure

A suspension of 3-[3-fluoro-4-(2-methoxy-ethoxy)-phenyl]-1-trityl-5-nitro-1H-indazole 4 (2.8 g, 4.88 mmol) and catalytic amount of Pd on carbon (5 wt %, 0.5 g) in 120 mL of methanol/toluene (1:1) was stirred under a hydrogen atmosphere for 6 h and filtered through Celite. The filtrate was concentrated to provide 3-[3-fluoro-4-(2-methoxy-ethoxy)-phenyl]-1-trityl-1H-indazol-5-ylamine 5 (2.6 g) as an off-white solid.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8daf44dde4e943a8b0130d1ce7b8c0e3
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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