Benzenesulfonyl chloride → HCID 12096279, compound

HRID 915736Notes

Reaction equation

HRID 915736 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](=[N: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](=[N: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 2724254Sodium bis(trimethylsilyl)amideHCID 120962783-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 12096279HCID 12096279, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium bis(trimethylsilyl)amide (0.2 mL, 1M in THF, 0.23 mmol) was added to a solution of 3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-7-azaindole (24.9 mg, 0.12 mmol) in THF (2.5 mL) at −78° C. and the mixture stirred for 1 h. Benzene-sulfonyl chloride (30 μL, 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 (˜1 g). 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-benzenesulfonyl-7-azaindole (21.3 mg, 51%, HRMS-FAB+ for C19H19N3O2S: calculated MH+: 354.12762; found: 354.12896).

Workup

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

Sources & evidence

ORD record
ord-86807d2116334e8a950641e9e6e654c9
Source dataset
uspto-grants-2007_09
Patent number
US07268127B2

Reaction notes

Loading…