Acetic Anhydride → 1-(2-acetoxyethyl)-3-(3,5-di-tertiary butylphenyl)-1H-pyrazolo[3,4-b]pyridine

HRID 1382893Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][CH2:26][OH:27])[N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1O)([CH3:4])([CH3:3])[CH3:2].[C:28](OC(=O)C)(=[O:30])[CH3:29]>C1(C)C=CC=CC=1>[C:28]([O:27][CH2:26][CH2:25][N:18]1[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:24]2[C:16]([C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[C:9]([C:12]([CH3:14])([CH3:13])[CH3:15])[CH:8]=2)=[N:17]1)(=[O:30])[CH3:29]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 40 g of the compound of Example 43 in 320 ml of toluene is added 22 g of acetic anhydride under stirring, and refluxed for 8 hours. After completion of the reaction, the reaction mixture is cooled to 20° C., washed with 300 ml of water twice and dried over anhydrous sodium sulfate. The toluene is concentrated and the residue is recrystallized from ethanol and dried to give 37 g of 1-(2-acetoxyethyl)-3-(3,5-di-tertiary butylphenyl)-1H-pyrazolo[3,4-b]pyridine, melting at 115°-116° C.

Workup

temperaturerefluxed for 8 hours
customAfter completion of the reaction
washwashed with 300 ml of water twice
dry with materialdried over anhydrous sodium sulfate
concentrationThe toluene is concentrated
customthe residue is recrystallized from ethanol
customdried

Sources & evidence

ORD record: ord-3db335a915d04e1c83ac3dd8cedd4b8c
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04808620

Reaction notes

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