Cesium carbonate → 2-methyl-7-[(2S)-oxiranylmethoxy]-1H-indole

HRID 132591Notes

Reaction equation

HRID 132591 reaction equation
[N+](C1C=C(S([CH2:13][C@@H:14]2[CH2:16][O:15]2)(=O)=O)C=CC=1)([O-])=O.[CH3:17][C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[OH:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:17][C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[O:27][CH2:13][C@@H:14]1[CH2:16][O:15]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 187652222-methyl-1H-indol-7-olHCID 86760692(2S)-2{[(3-nitrophenyl)sulfonyl]methyl}oxirane

Product 1

HCID 865928342-methyl-7-[(2S)-oxiranylmethoxy]-1H-indoleYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2S)-2{[(3-nitrophenyl)sulfonyl]methyl}oxirane (39 mg, 0.15 mmol), 2-methyl-1H-indol-7-ol (15 mg, 0.1 mmol), caesium carbonate (Cs2CO3) (65 mg, 0.2 mmol) in DMF (1.5 mL) was kept on stirring at room temperature for 5 h. The reaction mixture was partitioned between ethylacetate and water, organic layer dried over sodium sulphate (Na2SO4), filtered and concentrated. The residue was purified by silica gel flash chromatography to give subtitled compound (12 mg).

Workup

  1. customThe reaction mixture was partitioned between ethylacetate and water, organic layer
  2. dry with materialdried over sodium sulphate (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-ce01862c7e46447a8add5ec4b9db9cc7
Source dataset
uspto-grants-2008_06
Patent number
US07388020B2

Reaction notes

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