Potassium Carbonate → HCID 86231808, compound

HRID 750678Notes

Reaction equation

HRID 750678 reaction equation
[C:1]([O-])([O-])=[O:2].[K+].[K+].[CH:7]([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[CH3:18])=O.BrC[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CN(C=O)C.CCOC(C)=O>[C:24]([O:23][C:21](=[O:22])[CH2:7][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:1]=[O:2])=[C:10]1[CH3:18])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 12377726HCID 12377726, compound

Product 1

HCID 86231808HCID 86231808, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

K2CO3 (15 mmol, 2.07g) and 1-formyl-2-methyl indole (10 mmol, 1.59 g) were stirred in 50 mL DMF. t-Butyl bromoacetate (12 mmol, 1.77 mL) was added and the reaction was heated to 80° C. for 1 h. The reaction was cooled, diluted with 100 mL EtOAc, and washed with water (3×50 mL). The organic solution was dried over MgSO4 and concentrated to give the sub-title compound as a yellow solid (2.6 g).

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with water (3×50 mL)
  3. dry with materialThe organic solution was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0bc6991ff92744b0bad469de2a464bde
Source dataset
uspto-grants-2008_07
Patent number
US07405215B2

Reaction notes

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