Water → Ethyl 2-((3-(3,5-dimethoxyphenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)oxy)acetate

HRID 402498Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:18]([CH3:20])=[CH:17][C:16](=[O:21])[NH:15][C:14]=3[N:13]([CH3:22])[N:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CCN(C(C)C)C(C)C.Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][C:16]([O:21][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:17][C:18]=3[CH3:20])[N:13]([CH3:22])[N:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of 3-(3,5-dimethoxyphenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (1.0 g, 3.34 mmol) in DMF (5 ml) were added DIPEA (1.17 ml, 6.68 mmol) and ethyl 2-bromoacetate (0.56 ml, 5.01 mmol). After stirring at 90° C. for 1 h the mixture was cooled to rt, water was added and extracted three times with CH2Cl2. The organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting crude product was purified by column chromatography (eluent 50% hexane in EtOAc) to yield 910 mg (71%) of the title compound. [1H-NMR (DMSO-d6, 600 MHz): δ 6.71 (d, 2H), 6.61 (s, 1H), 6.57 (br s, 1H), 4.98 (s, 2H), 4.18 (q, 2H), 3.91 (s, 3H), 3.78 (s, 6H), 2.37 (s, 3H), 1.21 (t, 3H); UPLC-MS RtJ=1.21 min; [M+H]+=386.1]

Workup

temperaturewas cooled to rt
extractionextracted three times with CH2Cl2
dry with materialThe organic phases were dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting crude product was purified by column chromatography (eluent 50% hexane in EtOAc)

Sources & evidence

ORD record: ord-6a1fd7c7724f43b3b9702c6ae39b1487
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742106B2

Reaction notes

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