Potassium Carbonate → HCID 86593875, compound

HRID 1271855Notes

Reaction equation

HRID 1271855 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[S:21][C:20]2[CH:22]=[CH:23][C:24]([OH:26])=[CH:25][C:19]=2[CH:18]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH3:41]>C(#N)C.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[S:21][C:20]2[CH:22]=[CH:23][C:24]([O:26][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH3:41])=[CH:25][C:19]=2[CH:18]=1)=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1235321-Bromo-3,6-dioxaheptaneHCID 69487009HCID 69487009, compound

Product 1

HCID 86593875HCID 86593875, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 77 mg (0.20 mmol) {2-[(5-Hydroxy-benzo[b]thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (4) in 3 ml acetonitrile was added 200 mg potassium carbonate and 0.3 ml 1-bromo-2-(2-methoxyethoxy)-ethane. The reaction mixture was heated at 100° C. for 90 min and poured into brine. The aqueous phase was extracted with ethyl acetate and the organic phase was dried over sodium sulfate, the solvent was evaporated and the residue subjected to silica gel chromatography (petrolether/ethyl acetate 2:1 and then 1:1). The product (28) (80 mg, 0.164 mmol) was obtained as a colorless oil.

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1b4820037f0e4f3cb1c264e85d153b3a
Source dataset
uspto-grants-2007_04
Patent number
US07208491B2

Reaction notes

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