HCID 66766929, compound → HCID 66766885, compound

HRID 1661994Notes

Reaction equation

HRID 1661994 reaction equation
[F:1][C:2]1[CH:32]=[C:31]([N+:33]([O-])=O)[CH:30]=[CH:29][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]([NH:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:15])[N:10]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[N:9]=[CH:8]2>CO.[Pd]>[NH2:33][C:31]1[CH:30]=[CH:29][C:3]([O:4][C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][C:13]=2[C:14]([NH:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:15])[N:10]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[N:9]=[CH:8]3)=[C:2]([F:1])[CH:32]=1

Participants

4

Reactant 1

HCID 66766929HCID 66766929, compound

Product 1

HCID 66766885HCID 66766885, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-(2-fluoro-4-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-N-(tetrahydro-2H-pyran-4-yl)-1H-indazole-6-carboxamide (0.49 g, 1.0 mmol) in MeOH (50 mL) is added Pd/C (100 mg, 10% wt) under N2. The resulting mixture is degassed by evacuation and backfilled with nitrogen. Then the reaction mixture is stirred at RT under H2 atmosphere overnight. The solid is removed by filtration and the filtrate is concentrated to give a crude product (0.42 g, 91.4% yield). MS (m/z): 455.1 (M+H).

Workup

  1. customThe resulting mixture is degassed by evacuation
  2. customThe solid is removed by filtration
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-6dfbd450b04c471ab32768c565d205de
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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