Cesium carbonate → Ethyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]-2,2-dimethylpropanoate

HRID 2189800Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:14]=[C:13]([C:15]4[CH:16]=[CH:17][C:18]([O:23][CH:24]([CH3:26])[CH3:25])=[C:19]([CH:22]=4)[C:20]#[N:21])[O:12][N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.Br[CH2:28][C:29]([CH3:36])([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O.CCOC(C)=O>[C:20]([C:19]1[CH:22]=[C:15]([C:13]2[O:12][N:11]=[C:10]([C:6]3[CH:5]=[C:4]4[C:9](=[CH:8][CH:7]=3)[N:1]([CH2:28][C:29]([CH3:36])([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:2]=[CH:3]4)[N:14]=2)[CH:16]=[CH:17][C:18]=1[O:23][CH:24]([CH3:26])[CH3:25])#[N:21]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-[3-(1H-indazol-5-yl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile (D43) (85 mg, 0.246 mmol) in N,N-Dimethylformamide (DMF) (5 ml) was added ethyl 3-bromo-2,2-dimethylpropanoate (D98) (103 mg, 0.492 mmol) and Cs2CO3 (120 mg, 0.369 mmol). The resulting mixture was stirred at 80° C. for 48 h then cooled to room temperature and diluted with EtOAc. The organic phase was washed with water, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel [30-50% EtOAc/cyclohexene] gave the title compound (20 mg, 16%) as a yellow solid. MS (ES) C26H27N5O4 requires 473, found 474 [M+H]+

Workup

temperaturethen cooled to room temperature
washThe organic phase was washed with water
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customPurification of the residue by flash chromatography on silica gel [30-50% EtOAc/cyclohexene]

Sources & evidence

ORD record: ord-e1a9cd9717d2430680476f7dcec54ba8
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324254B2

Reaction notes

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