HCID 86602412, compound → HCID 69182765, compound

HRID 2373231Notes

Reaction equation

[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH:26]=[O:27])=[C:10]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[CH3:28][Mg]Br>C1COCC1.[Cl-].[NH4+]>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH:26]([OH:27])[CH3:28])=[C:10]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of ethyl 3-[1-ethyl-6-formyl-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]propanoate (42 mg) in THF (1 ml) was added 0.93M methylmagnesium bromide in THF (0.18 ml) at 0° C. and the reaction mixture was stirred at 0° C. for 1 hour. Another 0.93M methylmagnesium bromide in THF (0.18 ml) was added at 0° C. and the reaction mixture was stirred at 0° C. for 1 hour. The reaction mixture was diluted with saturated aqueous ammonium chloride and extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (3:1) to give ethyl 3-[1-ethyl-6-(1-hydroxyethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]propanoate (34 mg) as a colorless oil.

Workup

stirringthe reaction mixture was stirred at 0° C. for 1 hour
extractionextracted with EtOAc
washThe organic layer was washed with water, brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by preparative thin layer chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (3:1)

Sources & evidence

ORD record: ord-74ddc1a6abbb49798af2d525f9d7de79
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459451B2

Reaction notes

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