Benzenesulfonyl chloride → HCID 66850754, compound

HRID 1810196Notes

Reaction equation

HRID 1810196 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:18][CH2:17][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=[O:5])[CH3:2].[OH-].[Na+].[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:18][CH2:17][C:9]2[N:10]([S:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:29])=[O:28])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 1756750Ethyl 1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Product 1

HCID 66850754HCID 66850754, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3 g of 1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester in methylene chloride (50 mL) is treated with 0.982 g of sodium hydroxide and stirred and room temperature overnight. Benzenesulfonylchloride (6.30 mL) is added to the reaction and stirred at room temperature overnight. The reaction mixture is diluted with water (250 mL) and extracted with methylene chloride. The organics are combined, washed with water then a saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo The residue is loaded on Celite and purified by silica gel chromatography (1:1 hexanes/ethyl acetate) to give 5-benzenesulfonyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester as a yellow powder. MS (m/z): 385 (M+1).

Workup

  1. stirringstirred at room temperature overnight
  2. extractionextracted with methylene chloride
  3. washwashed with water
  4. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  5. concentrationconcentrated in vacuo The residue
  6. custompurified by silica gel chromatography (1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-7402ae3c0061434bb941b978a188c9f7
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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