Methanesulfonyl chloride → HCID 46944829, compound

HRID 506031Notes

Reaction equation

HRID 506031 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, is dissolved in pyridine (550 μL) at room temperature. Methanesulfonyl chloride (17 μL, 0.21 mmol) is added dropwise. This is stirred overnight at room temperature. The reaction mixture is then diluted in ethyl acetate and is washed with aqueous HCl, followed by brine. The organic layer is dried and concentrated. Purification by silica gel chromatography (9/1, CH2Cl2/EtOAc) yields N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-ylethynyl)-phenyl]-methanesulfonamide (58 mg, 92%) as an off-white solid.

Workup

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

Sources & evidence

ORD record
ord-a5344bc386264049814f75f6d2ab1e6b
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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