2-Methoxypropene → HCID 67501414, compound

HRID 1625269Notes

Reaction equation

N[C:2]1[CH:10]=[C:9]([N:11]2[C:15]3=[N:16][CH:17]=[CH:18][C:19]([I:20])=[C:14]3[C:13]([C:21]([F:24])([F:23])[F:22])=[N:12]2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO[C:41]([CH3:43])=[CH2:42].O.C(=O)(O)[O-].[Na+]>ClC(Cl)C.C(O)(=O)C.C(OCC)(=O)C>[I:20][C:19]1[CH:18]=[CH:17][N:16]=[C:15]2[N:11]([C:9]3[CH:8]=[CH:7][C:3]([C:4]([NH2:6])=[O:5])=[C:2]([CH:41]([CH3:43])[CH3:42])[CH:10]=3)[N:12]=[C:13]([C:21]([F:23])([F:24])[F:22])[C:14]=12

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

washthe organic layer was washed with saturated saline
dry with materialwas dried over anhydrous sodium sulfate
distillationThe solvent was distilled away

Sources & evidence

ORD record: ord-5987ee0e06074f60875d2cf73264f30f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779142B2

Reaction notes

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