Methanesulfonyl chloride → HCID 46944829, compound

HRID 907131Notes

Reaction equation

HRID 907131 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[N:11]([CH2:23][CH3:24])[C:12]3[C:17]([C:18]=2[C:19]#[N:20])=[CH:16][CH:15]=[C:14]([O:21][CH3:22])[CH:13]=3)=[CH:4][CH:3]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1.C(OCC)(=O)C>[C:19]([C:18]1[C:17]2[C:12](=[CH:13][C:14]([O:21][CH3:22])=[CH:15][CH:16]=2)[N:11]([CH2:23][CH3:24])[C:10]=1[C:9]#[C:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:26]([CH3:25])(=[O:28])=[O:27])=[CH:3][CH:4]=1)#[N:20]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11587731HCID 11587731, compound

Product 1

HCID 46944829HCID 46944829, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Aminophenylethynyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (50 mg, 0.16 mmol), prepared as described by the method of Example 1H, was dissolved in pyridine (550 μL) at room temperature. Methanesulfonyl chloride (17 μL, 0.21 mmol) was added dropwise. This was stirred overnight at room temperature. The reaction mixture was then diluted in ethyl acetate and was washed with aqueous HCl, followed by brine. The organic layer was dried and concentrated. Purification by silica gel chromatography (9/1, CH2Cl2/EtOAc) yielded N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-ylethynyl)-phenyl]-methanesulfonamide (58 mg, 92%) as an off-white solid.

Workup

  1. washwas washed with aqueous HCl
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (9/1, CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-f0b0d3c129a449ff85c2e4ca934589e0
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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