Potassium Carbonate → ethyl 2-(4-bromo-1H-indazol-1-yl)-3-(tetrahydro-2H-pyran-4-yl)propanoate

HRID 1802883Notes

Reaction equation

HRID 1802883 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.Br[CH:12]([CH2:18][CH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[C:13]([O:15][CH2:16][CH3:17])=[O:14].O1CCC(C=CC(OCC)=O)CC1.C(=O)([O-])[O-].[K+].[K+]>O.CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:12]([CH2:18][CH:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1)[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 223525484-bromo-1H-indazoleHCID 54040092ethyl 3-(tetrahydro-2H-pyran-4-yl)-2-propenoateHCID 58380608ethyl 2-bromo-3-(tetrahydro-2H-pyran-4-yl)propanoate

Product 1

HCID 58380603ethyl 2-(4-bromo-1H-indazol-1-yl)-3-(tetrahydro-2H-pyran-4-yl)propanoateYield 53.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromo-1H-indazole (3.00 g), a 1:1 mixture (6.73 g) of ethyl 2-bromo-3-(tetrahydro-2H-pyran-4-yl)propanoate and ethyl 3-(tetrahydro-2H-pyran-4-yl)-2-propenoate, potassium carbonate (2.1 g) and N,N-dimethylformamide (20 mL) was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to give the title compound (3.10 g) as a yellow oil from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio). MS: 383 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4aebe3ada0634d6e9e9b7d845e3a9883
Source dataset
uspto-grants-2013_01
Patent number
US08349886B2

Reaction notes

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