Ethanol → HCID 22504365, compound

HRID 1814145Notes

Reaction equation

HRID 1814145 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:15]=[C:10]3[CH:9]=[C:8]2[C:20]2[C:25]([F:26])=[C:24](Cl)[N:23]=[CH:22][N:21]=2)=[CH:4][CH:3]=1.C(O)C>[Pd].C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([S:16]([CH3:19])(=[O:17])=[O:18])[CH:15]=[C:10]3[CH:9]=[C:8]2[C:20]2[C:25]([F:26])=[CH:24][N:23]=[CH:22][N:21]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 22504366HCID 22504366, compound

Product 1

HCID 22504365HCID 22504365, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture of 1-(4-fluorobenzyl)-5-methanesulfonyl-2-(6-chloro-5-fluoropyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine obtained in Example 36 (5) (12 mg), ethanol (1 ml), ethyl acetate (1 ml) and 10% palladium on carbon (10 mg) was stirred under hydrogen stream at 15 to 30° C. for 1.5 hour. The catalyst was filtered through Celite. The filtrate was concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (methanol:dichloromethane=1:99) to obtain the desired product (9 mg) as a white powder.

Workup

  1. filtrationThe catalyst was filtered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was separated

Sources & evidence

ORD record
ord-1bc9d8bf78444009ae4f241de1f6b1d6
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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