Methanesulfonyl chloride → HCID 59425701, compound

HRID 502182Notes

Reaction equation

HRID 502182 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH2:24][CH3:25])[C:13]3[C:18]([C:19]=2[C:20]#[N:21])=[CH:17][CH:16]=[C:15]([O:22][CH3:23])[CH:14]=3)=[CH:7][CH:6]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>N1C=CC=CC=1>[C:20]([C:19]1[C:18]2[C:13](=[CH:14][C:15]([O:22][CH3:23])=[CH:16][CH:17]=2)[N:12]([CH2:24][CH3:25])[C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:1][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:6][CH:7]=1)#[N:21]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 59425830HCID 59425830, compound

Product 1

HCID 59425701HCID 59425701, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-[4-(2-Aminoethoxy)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (30 mg, 0.09 mmol), prepared in step B, above, is dissolved in pyridine (300 μL). Methanesulfonyl chloride (8 μL, 0.1 mmol) is added. This is stirred at room temperature for 45 minutes. More methanesulfonyl chloride (4 μL, 0.05 mmol) is added. Stirring continues for another hour. The reaction mixture is partitioned between EtOAc and aqueous HCl. The organic layer is dried and concentrated. Purification by silica gel chromatography (1/1 CH2Cl2/EtOAc) yields N-{2-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)phenoxy]ethyl}methanesulfonamide, compound 268 (32 mg, 86%) as a white solid.

Workup

  1. stirringStirring
  2. waitcontinues for another hour
  3. customThe reaction mixture is partitioned between EtOAc and aqueous HCl
  4. customThe organic layer is dried
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (1/1 CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-07e158753e404a1cbc82276e6024dde9
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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