Methanol → 3-(pyridin-4-yl)-1-trityl-1H-indazol-5-amine

HRID 1842046Notes

Reaction equation

HRID 1842046 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[N:8]=[C:7]2[C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1)([O-])=O.CO>[Pd].C(OCC)(=O)C>[N:35]1[CH:36]=[CH:37][C:32]([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([NH2:1])[CH:5]=3)[N:9]([C:13]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:8]=2)=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 601460255-nitro-3-(pyridin-4-yl)-1-trityl-1H-indazole

Product 1

HCID 576858103-(pyridin-4-yl)-1-trityl-1H-indazol-5-amineYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 5-nitro-3-(pyridin-4-yl)-1-trityl-1H-indazoie (0.8954 g, 0.00185 mol), 10% activated palladium on carbon (0.8954 g, 1 eq by weight) was added. The reaction flask was put under vacuum, and methanol (18.5 mL) and ethyl acetate (2 mL) was added. Hydrogen gas was bubbled through the reaction for 15 minutes. The reaction was stirred at room temperature for and additional 16 h. The reaction was filtered through celite and concentrated under vacuo. The crude product (0.819 g, 95% yield) was progressed to the next step without further purification.

Workup

  1. additionwas added
  2. customHydrogen gas was bubbled through the reaction for 15 minutes
  3. filtrationThe reaction was filtered through celite
  4. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-904b3bcf50384f8980cb5db21bcc73f5
Source dataset
uspto-grants-2015_02
Patent number
US08946216B2

Reaction notes

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