Potassium Carbonate → HCID 57475959, compound

HRID 1851418Notes

Reaction equation

HRID 1851418 reaction equation
COC[N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH:6]=[C:5]1[C:22]([NH2:24])=[O:23].Br[CH2:26][CH2:27][O:28][CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+].O.O.C(O)(=O)C(O)=O>C(OCC)(=O)C.[Cl-].[Na+].O.O.CO.CN(C)C=O>[CH2:27]([O:28][CH2:29][CH2:30][N:13]([S:14]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:16])[C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[NH:4][C:5]([C:22]([NH2:24])=[O:23])=[CH:6]2)[CH3:26]

Participants

10

Reactant 4

HCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl etherHCID 61373Oxalic acid dihydrateHCID 57475954HCID 57475954, compound

Product 1

HCID 57475959HCID 57475959, compoundYield 95%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 1-(methoxymethyl)-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (6.25 g), 1-bromo-2-ethoxyethane (3.41 g), potassium carbonate (7.09 g) and N,N-dimethylformamide (30 mL) was stirred at 75° C. for 6 hr. The reaction mixture was diluted with ethyl acetate and saturated brine. The organic layer was washed with aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate and filtrated. The filtrate was concentrated, subjected to NH silica gel column chromatography, and eluted with an ethyl acetate.hexane (2:1) mixture to give a solid. A mixture of this solid (5.50 g), oxalic acid dihydrate (4.77 g), methanol (50 mL) and water (50 mL) was stirred at 90° C. for 14 hr. The reaction mixture was cooled to room temperature and diluted with water. The crystallized solid was washed with water to give the title compound (4.70 g, yield 95%) as crystals. melting point 135° C.

Workup

  1. washThe organic layer was washed with aqueous sodium bicarbonate and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltrated
  4. concentrationThe filtrate was concentrated
  5. washeluted with an ethyl acetate
  6. customhexane (2:1) mixture to give a solid
  7. stirringwas stirred at 90° C. for 14 hr
  8. temperatureThe reaction mixture was cooled to room temperature
  9. washThe crystallized solid was washed with water

Sources & evidence

ORD record
ord-fb8e113ac93a45b8bf766b06add37d8c
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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