Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Methoxypropene | HCID 8300 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 67501494 | HCID 67501494 | — |
| Reactant | Sodium bicarbonate water | HCID 86585896 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | 1,1-Dichloroethane | HCID 6365 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67501414 | HCID 67501414 | 30% |
Reaction Steps
Compound (157a) (0.200 g), sodium triacetoxyborohydride (0.189 g), and isopropenyl methyl ether (0.102 mL) were dissolved in dichloroethane (2.0 mL) and acetic acid (0.50 mL), followed by stirring at 0° C. for 1 hr. The reaction solution was distributed between ethyl acetate and saturated sodium bicarbonate water, and the organic layer was washed with saturated saline and was dried over anhydrous sodium sulfate. The solvent was distilled away to obtain 4-{4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(isopropyl)benzamide, which was used in the subsequent reaction without being purified. According to Example 99(2), compound (160) (the second stage yield: 30%) was prepared as a white solid using 4-{4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(isopropyl)benzamide instead of compound (99a).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08779142B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-5987ee0e06074f60875d2cf73264f30f |
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| Source note | uspto-grants-2014_07 |
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