Methanol → HCID 57477566, compound

HRID 44914Notes

Reaction equation

HRID 44914 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[CH:8]=2)=[CH:5][N:4]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:21]=[CH:22][C:15]=23)[N:3]=1.CO.[BH4-].[Na+]>[Pd]>[CH3:1][C:2]1[C:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH:9]([OH:13])[CH2:8]2)=[CH:5][N:4]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:30])[CH3:29])[CH:21]=[CH:22][C:15]=23)[N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 578814203-[3-methyl-1-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-4-yl]cyclohex-2-en-1-one

Product 1

HCID 57477566HCID 57477566, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 3-[3-methyl-1-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-4-yl]cyclohex-2-en-1-one (0.019 g, 0.000045 mol) and palladium on carbon (Pd/C) (0.018 g, 0.000017 mol) in methanol (2 mL, 0.05 mol) was degassed and was stirred under a hydrogen atmosphere overnight. An additional 48 mg of 10% Pd/C was added and stirred under a hydrogen atmosphere for 8 h. The palladium was filtered and the filtrate was stirred with sodium tetrahydroborate (0.032 g, 0.00084 mol) for 5 h. The reaction was purified by prep-HPLC to give 5 mg of the desired product. MS (M+H)+: 426.

Workup

  1. customwas degassed
  2. additionAn additional 48 mg of 10% Pd/C was added
  3. stirringstirred under a hydrogen atmosphere for 8 h
  4. filtrationThe palladium was filtered
  5. customThe reaction was purified by prep-HPLC

Sources & evidence

ORD record
ord-5e9a1dede01b4efa9344451b733950ce
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Reaction notes

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