Sodium hydride → Ethyl 3-(4-cyano-1H-indazol-1-yl)-2,2-dimethylpropanoate

HRID 2189795Notes

Reaction equation

[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]#[N:11])[C:4]=2[CH:3]=[N:2]1.[H-].[Na+].Br[CH2:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C)C=O>[C:10]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[N:2][N:1]2[CH2:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:11]

Participants

Conditions

Temperature: 80 °C

Procedure

1H-indazole-4-carbonitrile (commercially available from Insight Chemical Solutions Ltd., 298 mg, 1.957 mmol) in dry N,N-Dimethylformamide (DMF) (1 ml), under nitrogen was treated with NaH (94 mg, 2.348 mmol). A solution of ethyl 3-bromo-2,2-dimethylpropanoate (D98) (450 mg, 2.153 mmol), in DMF (2 ml), was then added to the dark brown mixture. The reaction mixture was heated to 80° C. overnight then concentrated in vacuo. The residue was dissolved in EtOAc and the organic phase was washed with water then brine, dried and concentrated to give a brown gum. Purification of the residue by flash chromatography on silica gel [gradient ethyl acetate/cyclohexane] gave the title compound (217 mg, 86%) as a yellow oil. MS (ES) C15H15N3O2 requires 271, found 272 [M+H]+

Workup

concentrationthen concentrated in vacuo
dissolutionThe residue was dissolved in EtOAc
washthe organic phase was washed with water
dry with materialbrine, dried
concentrationconcentrated
customto give a brown gum
customPurification of the residue by flash chromatography on silica gel [gradient ethyl acetate/cyclohexane]

Sources & evidence

ORD record: ord-83083710d34a4e93bedddcb670e85c2e
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324254B2

Reaction notes

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