Methanol → HCID 66803517, compound

HRID 1843986Notes

Reaction equation

HRID 1843986 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]3[CH2:13][CH2:14][NH:15][C:16](=[O:17])[C:7]=3[C:6]=2[CH:5]=1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CO>CN(C=O)C.C(Cl)Cl>[F:3][C:4]1[CH:12]=[CH:11][C:10]2[N:9]([S:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:26])=[O:25])[C:8]3[CH2:13][CH2:14][NH:15][C:16](=[O:17])[C:7]=3[C:6]=2[CH:5]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 19799247HCID 19799247, compound

Product 1

HCID 66803517HCID 66803517, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

60% NaH (196 mg, 8.16 mmol) was added to a stirred solution of 8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one (500 mg, 2.44 mmol) in DMF (20 mL) at −10° C. and stirred for 10 minutes at room temperature. This was followed by the addition of benzene sulfonyl chloride (517 mg, 2.92 mmol) at 0° C. and the resulting reaction mass was stirred at room temperature for 5 minutes. The reaction was monitored by TLC (5% methanol in DCM). The reaction mass was quenched with ice and extracted using ethyl acetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated to afford the crude product. Purification by column chromatography on silica gel (0.5% methanol in DCM) afforded 450 mg of the product (53.6% yield).

Workup

  1. customthe resulting reaction mass
  2. stirringwas stirred at room temperature for 5 minutes
  3. customThe reaction mass was quenched with ice
  4. extractionextracted
  5. washThe organic layer was washed with water, brine solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto afford the crude product
  9. customPurification by column chromatography on silica gel (0.5% methanol in DCM)

Sources & evidence

ORD record
ord-5cc11f60303144978e2d14f542d8edac
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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