Potassium Carbonate → Ethyl 3-[5-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]-2,2-dimethylpropanoate

HRID 2189803Notes

Reaction equation

HRID 2189803 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][N:21]=[CH:20]4)[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Br[CH2:27][C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[N:22]([CH2:27][C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:21]=[CH:20]4)[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12373576Ethyl 3-bromo-2,2-dimethylpropanoateHCID 532474905-(5-{5-Chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indazole

Product 1

HCID 59316809Ethyl 3-[5-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]-2,2-dimethylpropanoateYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indazole (D110) (335 mg, 0.94 mmol), ethyl 3-bromo-2,2-dimethylpropanoate (D98) (197 mg, 0.94 mmol) and K2CO3 (130 mg, 0.94 mmol) in DMF (5 ml) was stirred at 80° C. for 48 hours. The reaction mixture was then cooled to room temperature and partitioned between EtOAc and water (30 ml). The organic phase was separated, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel [20% ethyl acetate/cyclohexane] gave the title compound (100 mg, 22%) as a colourless solid. MS (ES) C24H26ClN5O4 requires 483, found 484 [M+H]+

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. custompartitioned between EtOAc and water (30 ml)
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography on silica gel [20% ethyl acetate/cyclohexane]

Sources & evidence

ORD record
ord-e7ab93a0465245009d4d720d22da1bf7
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

Loading…