Potassium Carbonate → HCID 57742340, compound

HRID 655302Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]1[N:17]3[N:18]=[CH:19][CH:20]=[N:21][C:16]3=[N:15][N:14]=1)=[CH:7][CH:6]=2.[CH3:22][N:23]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=[N:24]1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O>[CH3:22][N:23]1[CH:27]=[C:26]([C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][C:8]([CH2:12][C:13]2[N:17]4[N:18]=[CH:19][CH:20]=[N:21][C:16]4=[N:15][N:14]=2)=[CH:7][CH:6]=3)[CH:25]=[N:24]1

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of 3-bromo-6-[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-ylmethyl-quinoline (69 mg, 0.204 mmol), 1-methyl-4-pyrazoleboronic acid pinacol ester (51 mg, 0.25 mmol), potassium carbonate (56 mg. 0.41 mml), 1,4-dioxane (2 mL) and water (1 mL) was bubbled nitrogen gas through for 10 minutes. After such time dichlorobis(triphenylphosphine)palladium (8 mg, 5 mol %) was added, the vial sealed and heated in a microwave for 1500 seconds at 135° C. The mixture was diluted with dichloromethane and brine, before the organic phase was concentrated onto silica gel and via flash column chromatography (SiO2 4 g, dichloromethane/CH3OH 0-10%) to return the title compound a white solid (11 mg, 16%). Analytical data presented in Table 2.

Workup

customwas bubbled nitrogen gas through for 10 minutes
additionAfter such time dichlorobis(triphenylphosphine)palladium (8 mg, 5 mol %) was added
customthe vial sealed
additionThe mixture was diluted with dichloromethane and brine, before the organic phase
concentrationwas concentrated onto silica gel and via flash column chromatography (SiO2 4 g, dichloromethane/CH3OH 0-10%)

Sources & evidence

ORD record: ord-099c75a48e2d481d8021a2f8294b0e68
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071581B2

Reaction notes

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