Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl bromoacetate | HCID 7748 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 90237820 | HCID 90237820 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 90241399 | HCID 90241399 | 65% |
Reaction Steps
To a solution of tert-butyl 4-(5-hydroxy-1H-indazol-1-yl)piperidine-1-carboxylate (150 mg, 0.458 mmol) in DMF (10 mL) at 0° C. was added NaH (60% in mineral oil) (16.8 mg, 0.706 mmol) and ethyl 2-bromoacetate (119 mg, 0.706 mmol). The mixture was stirred at 25° C. for 3 h, poured into water, and the product extracted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4, concentrated under reduced pressure and purified by TLC (Pet.Ether:EtOAc=1:1) to give tert-butyl 4-(5-(2-ethoxy-2-oxoethoxy)-1H-indazol-1-yl)piperidine-1-carboxylate (120 mg, yield 65%) as a colorless oil. LCMS (m/z): 404.2 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09266836B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-ca332ecd999e40339f777ace6843b1d6 |
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| Source note | uspto-grants-2016_02 |
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