3-(2-Methoxy-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole → 3-(2-methoxypyridin-4-yl)-1-trityl-1H-indazol-5-ylamine

HRID 1020947Notes

Reaction equation

HRID 1020947 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=3)[N:11]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:10]=2)[CH:6]=[CH:5][N:4]=1>CO.C1(C)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=3)[N:11]([C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:10]=2)[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 1

HCID 673446273-(2-Methoxy-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole

Product 1

HCID 583720003-(2-methoxypyridin-4-yl)-1-trityl-1H-indazol-5-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21867641Toluene methanolSolvent

Procedure

To the stirred suspension of 3-(2-Methoxy-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole 4BV (5.125 g, 10.0 mmole) in MeOH/toluene (50 mL/50 mL) was added 10% Pd/C (Degussa type, 0.5 g) at r.t. under dry N2 gas. The mixture was degassed and was stirred under a balloon inflated with H2 gas overnight. The catalyst was filtered through microfiber filter and was washed with MeOH and CH2Cl2. The filtrate was evaporated to dryness and a brown solid 5BV was obtained (5.0 g).

Workup

  1. customThe mixture was degassed
  2. custominflated with H2 gas overnight
  3. filtrationThe catalyst was filtered through microfiber
  4. filtrationfilter
  5. washwas washed with MeOH and CH2Cl2
  6. customThe filtrate was evaporated to dryness
  7. customa brown solid 5BV was obtained (5.0 g)

Sources & evidence

ORD record
ord-311c9f53991841e99af52dc0f4531318
Source dataset
uspto-grants-2014_05
Patent number
US08716483B2

Reaction notes

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