Dimethyl Sulfate → tert-Butyl 2-[1-methyl-5-(phenylsulfonyl)-1H-indol-3-yl]ethylcarbamate

HRID 412995Notes

Reaction equation

HRID 412995 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[C:13]3[CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:29]([O-])([O-])=O.[Cs+].[Cs+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:29][N:15]1[C:16]2[C:12](=[CH:11][C:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:8])=[O:9])=[CH:18][CH:17]=2)[C:13]([CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[CH:14]1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 10796Cesium carbonateHCID 10135626HCID 10135626, compound

Product 1

HCID 10273245tert-Butyl 2-[1-methyl-5-(phenylsulfonyl)-1H-indol-3-yl]ethylcarbamateYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of tert-butyl 2-[5-(phenylsulfonyl)-1H-indol-3-yl]ethylcarbamate (0.58 g, 1.46 mmol) in acetone (25.0 mL) was treated with Cs2CO3 (1.85 g, 5.68 mmol) and dimethyl sulfate (0.80 mL, 8.45 mmol). The reaction was stirred at room temperature for 3.5 hours then filtered. The filtrate was concentrated in vacuo and subjected to column chromatography (silica gel, 30% EtOAc/hexane) to give 0.41 g (68%) of a colorless solid as the title compound: mp 127.4-130.6° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.22 (s, 1H), 7.93 (d, J=7.1 Hz, 1H), 7.65-7.55 (m, 5H), 7.35 (s, 1H), 6.93 (br, 1H), 3.77 (s, 3H), 3.20-3.18 (m, 2H), 2.86-2.82 (m, 2H), 1.37 (s, 9H); 13C NMR (100 MHz, DMSO-d6) δ 155.5, 142.7, 138.3, 132.8, 130.5, 130.0, 129.4, 127.0, 126.7, 119.7, 119.3, 113.4, 110.7, 77.4, 41.1, 32.5, 28.1, 24.9; IR (diffuse reflectance) 1676, 1531, 1450, 1366, 1316, 1303, 1286, 1177, 1152, 1144, 1103, 797, 726, 692, 626 cm−1; HRMS (FAB) calcd for C22H26N2O4S+H 414.1613, found 414.1619; Anal. Calcd for C22H26N2O4S: C, 63.74; H, 6.32; N, 6.76. Found: C, 63.78; H, 6.39; N, 6.80.

Workup

  1. filtrationthen filtered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e9607af1ee4e41c49d1a04e37bae6638
Source dataset
uspto-grants-2003_05
Patent number
US06565829B2

Reaction notes

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