Methanesulfonyl chloride → HCID 59425701, compound

HRID 907164Notes

Reaction equation

HRID 907164 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, was dissolved in pyridine (300 μL). Methanesulfonyl chloride (8 μL, 0.1 mmol) was added. This was stirred at room temperature for 45 minutes. More methansulfonyl chloride (4 μL, 0.05 mmol) was added. Stirring continued for another hour. The reaction mixture was partitioned between EtOAc and aqueous HCl. The organic layer was dried and concentrated. Purification by silica gel chromatography (1/1 CH2Cl2/EtOAc) yielded 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. waitcontinued for another hour
  3. customThe reaction mixture was partitioned between EtOAc and aqueous HCl
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (1/1 CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-3e0e241de9de4320a130ab5c979b4ccc
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

Loading…