tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allylcarbamate → HCID 57590905, compound

HRID 1783758Notes

Reaction equation

HRID 1783758 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[C:5]2=[N:13][NH:14][C:15](=[O:16])[N:4]2[CH:3]=1.[C:17]([O:21][C:22](=[O:36])[NH:23][CH2:24]/[CH:25]=[CH:26]/B1OC(C)(C)C(C)(C)O1)([CH3:20])([CH3:19])[CH3:18]>O1CCOCC1.C([O-])([O-])=O.[K+].[K+]>[C:17]([O:21][C:22](=[O:36])[NH:23][CH2:24]/[CH:25]=[CH:26]/[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[C:5]2=[N:13][NH:14][C:15](=[O:16])[N:4]2[CH:3]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 11818401tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allylcarbamateHCID 575908626-Bromo-9-chloro-1,2,4-triazolo[3,4-a]isoquinolin-3(2H)-one

Product 1

HCID 57590905HCID 57590905, compound

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

6-bromo-9-chloro[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (3-9) (60 mg, 0.201 mmol, 1.0 equiv.) and tert-butyl[(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]carbamate (3-3) (228 mg, 0.804 mmol, 4.0 equiv.) were dissolved in anhydrous 1,4-dioxane (0.6 ml) and 2 M K2CO3 aqueous solution (0.2 mL). The reaction mixture was heated to 100° C. LCMS at 18 hours showed complete conversion. Purification with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA) afforded the title product 3-10. LRMS m/z (M+H) 375.1 found, 375.1 required.

Workup

  1. customPurification with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA)

Sources & evidence

ORD record
ord-d866d13c699e425cadf4e782d6af76db
Source dataset
uspto-grants-2009_03
Patent number
US07501435B2

Reaction notes

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