Acetone → HCID 10369926, compound

HRID 746471Notes

Reaction equation

HRID 746471 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[CH:25]=[CH:24][NH:23][C:18]4=[N:19][C:20]=3[O:21][CH3:22])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[OH-:28].[K+].[Cl-].C[C:32]([CH3:34])=[O:33]>>[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:25]([C:34](=[O:28])[C:32]([N:23]5[CH2:24][CH2:25][CH2:17][CH2:18]5)=[O:33])=[CH:24][N:23]([CH2:20][O:21][CH3:22])[C:18]4=[N:19][C:20]=3[O:21][CH3:22])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 312ChlorideHCID 14797Potassium HydroxideHCID 59747887HCID 59747887, compound

Product 1

HCID 10369926HCID 10369926, compoundYield 77%

Procedure

To a solution of [4-(4-Fluoro-benzyl)-piperidin-1-yl]-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-5-yl)-methanone (150 mg, 0.41 mmol) and ground KOH (114 mg, 2 mmol) in anhydrous acetone (15 mL) was added MOM chloride (82 mg, 1 mmol) at 0° C. The reaction mixture was warmed to RT slowly and stirred overnight. The solvent was removed, and the residue was treated with water and extracted with EtOAc. The combined organic layer was washed with brine, dried and concentrated. The residue was purified by chromatography on silica gel eluting with EtOAc:hexane (1:1) to give the desired product 130 mg (77% yield) as a white solid. M+H+(411).

Workup

  1. customThe solvent was removed
  2. additionthe residue was treated with water
  3. extractionextracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel eluting with EtOAc:hexane (1:1)

Sources & evidence

ORD record
ord-b79f682f7f854c6883ffd423666f47c4
Source dataset
uspto-grants-2008_07
Patent number
US07393851B2

Reaction notes

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