Ethyl bromoacetate → HCID 67151458, compound

HRID 551497Notes

Reaction equation

HRID 551497 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:25]=[C:24]4[C:20]([CH:21]=[N:22][NH:23]4)=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)=[C:4]([O:26][CH3:27])[CH:3]=1.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C.O>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][N:23]1[C:24]2[C:20](=[CH:19][CH:18]=[C:17]([CH2:16][O:15][C:12]3[CH:11]=[CH:10][C:9]([C:5]4[CH:6]=[C:7]([F:8])[C:2]([F:1])=[CH:3][C:4]=4[O:26][CH3:27])=[CH:14][CH:13]=3)[CH:25]=2)[CH:21]=[N:22]1)[CH3:34]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 52939612HCID 52939612, compound

Product 1

HCID 67151458HCID 67151458, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

6-(4′,5′-Difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-1H-indazole (0.15 g, 0.331 mmol), ethyl bromoacetate (0.055 g, 0.331 mmol), cesium carbonate (119 mg, 0.364 mmol) in 6 mL DMF was stirred at RT overnight and then heated to 90° C. for 35 min. The reaction was cooled and distributed between EtOAc and H2O. The organic layer was separated and concentrated in vacuo. The crude product was purified by flash chromatography with a gradient from 0-30% ethyl acetate in hexanes to yield [6-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-indazol-1-yl]-acetic acid ethyl ester as a white solid (120 mg, 80.1%).

Workup

  1. temperatureThe reaction was cooled
  2. customThe organic layer was separated
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography with a gradient from 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2d61329f9ecc4171bd422cbf0a23b155
Source dataset
uspto-grants-2011_05
Patent number
US07947728B1

Reaction notes

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