Dimethylformamide → HCID 67093539, compound

HRID 1661656Notes

Reaction equation

HRID 1661656 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]3[CH:12]=[C:13]([O:17][S:18](=[O:25])(=[O:24])[N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:14]=[N:15][CH:16]=3)[NH:8]2)=[CH:4][CH:3]=1.[CH3:26]N(C=O)C.C(=O)(OC)OC.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]3[CH:12]=[C:13]([O:17][S:18](=[O:24])(=[O:25])[N:19]([CH2:20][CH3:21])[CH2:22][CH3:23])[CH:14]=[N:15][CH:16]=3)[N:8]2[CH3:26])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12021Dimethyl CarbonateHCID 67093668HCID 67093668, compound

Product 1

HCID 67093539HCID 67093539, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A flask is charged with diethyl-sulfamic acid 5-(6-chloro-1H-indol-2-yl)-pyridin-3-yl ester (0.175 g, 0.560 mmol) and DMF (5 mL). Dimethyl carbonate (0.116 mL, 1.38 mmol) and potassium carbonate (0.035 g, 0.253 mmol) are added and the reaction is stirred at 150° C. overnight. The reaction mixture is cooled to room temperature, diluted with ethyl acetate and washed with water. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by flash chromatography (heptane-ethyl acetate, 3:1) to afford diethyl-sulfamic acid 5-(6-chloro-1-methyl-1H-indol-2-yl)-pyridin-3-yl ester as a yellow solid. MS (ESI) m/z 394.04 (M+H)+

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography (heptane-ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-a9aec174a89a49c29f3f55b8c2cf6f8e
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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