Benzenesulfonyl chloride → HCID 9950402, compound

HRID 367373Notes

Reaction equation

HRID 367373 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][N:12]1[CH2:17][CH:16]=[C:15]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)[CH2:14][CH2:13]1.[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[CH3:11][N:12]1[CH2:13][CH:14]=[C:15]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([S:33]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:35])=[O:34])[CH:19]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 1522153-(1-Methyl-1,2,3,6-tetrahydropyrid-4-yl)indoleHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 9950402HCID 9950402, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium bis(trimethylsilyl)amide (0.23 mL, 1M inTHF, 0.23 mmol) was added to a solution of 3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)indole (Example 4e, 25.0 mg, 0.12 mmol) in THF (1.5 mL) at -78° C. and the mixture was stirred for 1 h. Phenylsulfonyl chloride (30 uL, 0.24 mmol) was added and the mixture stirred at room temperature for 2 h. prior to quenching with water (4 drops) and silica gel (~1g). Purification using solid phase extraction tubes (1000 mg silica, eluting with 0-10% 2M methanolic ammonia in dichloromethane) yielded 3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1-phenylsulfonylindole (9.0 mg, 22%, HRMS-FAB+ for C20H20N2O2S: calculated MH+ : 353.13239; found: 353.13235).

Workup

  1. stirringthe mixture stirred at room temperature for 2 h.
  2. customto quenching with water (4 drops) and silica gel (~1g)
  3. customPurification
  4. extractionsolid phase extraction tubes (1000 mg silica, eluting with 0-10% 2M methanolic ammonia in dichloromethane)

Sources & evidence

ORD record
ord-539b56de959f443ab464776b54beaf07
Source dataset
uspto-grants-2000_10
Patent number
US06133287

Reaction notes

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