Potassium Carbonate → HCID 67119616, compound

HRID 2080227Notes

Reaction equation

HRID 2080227 reaction equation
BrC1OC(CNC([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[CH:14]3)=O)=CC=1.NC1N=C(N)C=CC=1[C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31](COC2C=CC=CC=2)=CN=1)=[O:25].[C:47]1(B(O)O)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.C(=O)([O-])[O-:57].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O>[C:47]1([C:31]2[O:57][C:28]([CH2:27][NH:26][C:24]([C:16]3[CH:15]=[CH:14][C:13]4[C:18](=[CH:19][CH:20]=[CH:11][CH:12]=4)[N:17]=3)=[O:25])=[CH:33][CH:32]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 23130550HCID 23130550, compoundHCID 58388006HCID 58388006, compound

Product 1

HCID 67119616HCID 67119616, compoundYield 33%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of quinoline-6-carboxylic acid (5-bromo-furan-2-ylmethyl)-amide described in Preparation Example E+-2 (200 mg, 0.60 mmol) in 1,4-dioxane (5 mL) were added phenylboronic acid (150 mg, 1.2 mmol), tetrakis(triphenylphosphine)palladium(0) (55 mg, 0.047 mmol) and an aqueous solution of potassium carbonate (2 mol), and the solution was stirred at 110° C. for 2 hours. Water and ethyl acetate were added to the reaction solution, which was then partitioned, NH silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, purification was carried out by NH silica gel column chromatography (hexane:ethyl acetate=2:1), and the title compound (65 mg, 0.198 mmol, 33.0%) was obtained as a white solid.

Workup

  1. customwas then partitioned
  2. additionNH silica gel was added to the organic layer
  3. customthe solvent was evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record
ord-28b019308883404c845c362e922c3949
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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