Ethyl bromoacetate → HCID 11720177, compound

HRID 1042569Notes

Reaction equation

HRID 1042569 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]2[C:7]([C:15]([C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=3)=[O:16])=[C:8]([C:10]3[CH:11]=[N:12][NH:13][CH:14]=3)[O:9][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>CN(C=O)C>[CH2:42]([O:41][C:39](=[O:40])[CH2:38][N:13]1[CH:14]=[C:10]([C:8]2[O:9][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:30]=[CH:29][C:6]=3[C:7]=2[C:15](=[O:16])[C:17]2[CH:18]=[C:19]([O:27][CH3:28])[C:20]([O:25][CH3:26])=[C:21]([O:23][CH3:24])[CH:22]=2)[CH:11]=[N:12]1)[CH3:43]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 11661458HCID 11661458, compound

Product 1

HCID 11720177HCID 11720177, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of [6-Methoxy-2-(1H-pyrazol-4-yl)-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone (45 mg, 0.091 mmol) and potassium carbonate (40 mg, 0.29 mmol) in dry DMF (2.5 mL) was added ethyl bromoacetate (30 μL, 0.27 mmol) and the reaction heated to 70° C. for 2 h. After cooling to room temperature the reaction mixture was quenched with 10% NH4Cl(aq) (20 mL) and extracted with ethyl acetate (30 mL). The organic layer was separated and washed with water (3×10 mL) and brine (10 mL), dried over magnesium sulphate and the solvent removed under reduced pressure. The crude residue was purified by flash column chromatography (silica gel, eluent=2:1 hexane:ethyl acetate) to give the title compound as a yellow solid (44 mg, 98%). 1H-NMR (CDCl3) δ 8.28 (s, 1H), 8.06 (s, 1H), 7.13 (s, 2H), 7.10 (d, J=8.7 Hz, 1H), 7.04 (d, J=2.1 Hz, 1H), 6.79 (dd, J=8.7, 2.1 Hz, 1H), 4.91 (s, 2H), 4.23 (q, J=7.1 Hz, 2H), 3.93 (s, 3H), 3.86 (s, 3H), 3.77 (s, 6H), 1.27 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas quenched with 10% NH4Cl(aq) (20 mL)
  3. extractionextracted with ethyl acetate (30 mL)
  4. customThe organic layer was separated
  5. washwashed with water (3×10 mL) and brine (10 mL)
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed under reduced pressure
  8. customThe crude residue was purified by flash column chromatography (silica gel, eluent=2:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-d3acfd5f815d4a11970b11cd7588ea92
Source dataset
uspto-grants-2013_10
Patent number
US08557982B2

Reaction notes

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