Potassium Carbonate → HCID 69490339, compound

HRID 1271869Notes

Reaction equation

HRID 1271869 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.Br[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1>C(OCC)(=O)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][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=3)=[CH:25][C:19]=2[CH:18]=1)=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 69487009HCID 69487009, compound

Product 1

HCID 69490339HCID 69490339, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

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 ethyl acetate was added 200 mg potassium carbonate and 56 mg (0.22 mmol) 2-(bromomethyl)pyridine, hydrobromide. The reaction mixture was heated at reflux for 10 h 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 3:2) to yield (2-{[5-(Pyridin-2-ylmethoxy)-benzo[b]thiophene-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester (52) (80 mg, 0.168 mmol) as colorless crystals.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 10 h
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a11a84733380483dada1489c0ec600ba
Source dataset
uspto-grants-2007_04
Patent number
US07208491B2

Reaction notes

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