Potassium Carbonate → HCID 70974927, compound

HRID 517093Notes

Reaction equation

HRID 517093 reaction equation
Br[C:2]1[C:7]([CH2:8][N:9]2[N:18]=[CH:17][C:16]3[C:11](=[CH:12][C:13]([C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=4)=[CH:14][CH:15]=3)[C:10]2=[O:30])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:31]1(B(O)O)[CH2:33][CH2:32]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH:31]1([C:2]2[C:7]([CH2:8][N:9]3[N:18]=[CH:17][C:16]4[C:11](=[CH:12][C:13]([C:19]5[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=5)=[CH:14][CH:15]=4)[C:10]3=[O:30])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 71467551HCID 71467551, compound

Product 1

HCID 70974927HCID 70974927, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-((2-bromopyridin-3-yl)methyl)-7-(4-(trifluoromethoxy)phenyl)phthalazin-1(2H)-one (25 mg, 0.053 mmol), cyclopropyl boronic acid (14 mg, 0.16 mmol), dppf(Pd)Cl2 (6 mg, 0.0079 mmol), potassium carbonate (29 mg, 0.021 mmol) in degassed dioxane (1 mL) was heated at 100° C. for 3 hours. The layers were separated, the organic layer was concentrated and the residue was purified by reverse phase HPLC to provide 2-((2-cyclopropylpyridin-3-yl)methyl)-7-(4-(trifluoromethoxy)phenyl)phthalazin-1(2H)-one as a white powder. C24H18F3N3O2. 438.1 (M+1).

Workup

  1. customThe layers were separated
  2. concentrationthe organic layer was concentrated
  3. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-ad34cd097c9f4989822ca93e76ebfa3e
Source dataset
uspto-grants-2015_08
Patent number
US09115096B2

Reaction notes

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