Benzenesulfonyl chloride → HCID 12085355, compound

HRID 1166191Notes

Reaction equation

HRID 1166191 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][CH2:14][CH:13]=1.[H-].[Na+].[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:33]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:35])=[O:34])[CH:6]=[C:5]2[CH2:11][C:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][CH2:14][CH:13]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 12085354HCID 12085354, compound

Product 1

HCID 12085355HCID 12085355, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of tert-butyl 5-[(5-fluoro-1H-indol-3-yl)methyl]-3,6-dihydro-1(2H)-pyridinecarboxylate (430 mg, 1.30 mmol) in tetrahydrofuran is treated with NaH (60% in mineral oil, 78 mg, 1.95 mmol) portion-wise under nitrogen at room temperature, stirred for 0.5 hr, treated with benzenesulfonyl chloride (0.25 ml, 1.95 mmol), stirred for 17 hr under nitrogen at room temperature, quenched with ice-water and diluted with ethyl acetate. The phases are separated and the aqueous phase is extracted with ethyl acetate. The combined extracts and organic phase are washed with water and saturated NaCl, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane, 1/9) to afford the title compound as a yellow solid, 350 mg, mp 63-65° C., identified by NMR and mass spectral analyses.

Workup

  1. stirringstirred for 17 hr under nitrogen at room temperature
  2. customquenched with ice-water
  3. additiondiluted with ethyl acetate
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with ethyl acetate
  6. washThe combined extracts and organic phase are washed with water and saturated NaCl
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane, 1/9)

Sources & evidence

ORD record
ord-3d07f12a7b644716b0349328659bd029
Source dataset
uspto-grants-2003_09
Patent number
US06613781B2

Reaction notes

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