Sulfur Dioxide → 1-Methylindole-2-sulfonyl chloride

HRID 1166861Notes

Reaction equation

HRID 1166861 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[Li]C(C)(C)C.[S:16](=[O:18])=[O:17].C1C(=O)N([Cl:26])C(=O)C1>C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[S:16]([Cl:26])(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 1119Sulfur DioxideHCID 117811-MethylindoleHCID 31398ChlorosuccinimideHCID 178418306HCID 178418306, compound

Product 1

HCID 229985021-Methylindole-2-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Methylindole-2-sulfonyl chloride was prepared by the method of Example 34 with 1-methylindole (7.8 mmols, 1.0 ml), t-BuLi (1.7 m, 9.4 mmols, 5.5 ml), sulfur dioxide, NCS (8.6 mmols, 1.2 g) and THF (15 ml). Flash chromatography (2% ethyl acetate/hexanes) provided 0.66 g (36%) of a yellow solid.

Sources & evidence

ORD record
ord-a5c9f835b51b4e38a7f01e82f73be964
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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