Methanesulfonyl chloride → HCID 59425201, compound

HRID 502243Notes

Reaction equation

HRID 502243 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[CH:19]2)[CH3:2].[CH3:25][S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1.O>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([S:26]([CH3:25])(=[O:28])=[O:27])[CH:20]=[CH:19]2)[CH3:2]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59426180HCID 59426180, compound

Product 1

HCID 59425201HCID 59425201, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 1-ethyl-6-methoxy-1H,1′H-[2,5′]biindolyl-3-carbonitrile (70 mg, 0.22 mmol), prepared as described in Example 1Gb, in pyridine (2 mL) is treated with methanesulfonyl chloride (0.034 mL, 0.44 mmol) and stirred overnight. The reaction mixture is then diluted with H2O and extracted with ethyl acetate (3×). The organic phase is washed with H2O and saturated NaCl, dried and concentrated and purified by flash chromatography using EtOAc/hexanes (30-80%) to afford 70 mg (81%) of 1-ethyl-1′-methanesulfonyl-6-methoxy-1H,1′H-[2,5′]biindolyl-3-carbonitrile as a tan solid.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe organic phase is washed with H2O and saturated NaCl
  3. customdried
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-473bd4f4c6aa49a2a82b2d8b25818da5
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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