Potassium Carbonate → HCID 46841560, compound

HRID 1846340Notes

Reaction equation

HRID 1846340 reaction equation
[CH:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:22]2[CH:23]=[N:24][C:25](Cl)=[CH:26][CH:27]=2)=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2].[CH3:29]B1OB(C)OB(C)O1.C([O-])([O-])=O.[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>[CH:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:22]2[CH:23]=[N:24][C:25]([CH3:29])=[CH:26][CH:27]=2)=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 46841412HCID 46841412, compound

Product 1

HCID 46841560HCID 46841560, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

3-(4-sec-butylphenyl)-2-(6-chloropyridin-3-yl)quinazolin-4(3H)-one (0.345 g, 0.89 mmol), trimethyboroxine (0.124 mL, 0.89 mmol), Pd(PPh3)4 (0.102 g, 0.09 mmol), and K2CO3 (0.368 g, 2.67 mmol) were combined in dioxane (10 mL) and heated at reflux under nitrogen for 5 hours. The reaction mixture was cooled to room temperature, filtered through Celite®, with THF washings, concentrated, and purified by flash chromatography on silica gel, eluting with 50% ethyl acetate/heptane to 100% ethyl acetate, to afford the title compound as a white solid (0.195 g, 59%). 1H-NMR (300 MHz, DMSO-6): δ 8.43 (d, J=2.0 Hz, 1H), 8.20 (d, J=6.9 Hz, 1H), 7.89-7.94 (m, 1H), 7.79 (d, J=7.9 Hz, 1H), 7.55-7.65 (m, 2H), 7.13-7.27 (m, 4H), 7.07 (d, J=8.1 Hz, 1H), 2.55-2.60 (m, 1H), 2.36 (s, 3H), 1.37-1.58 (m, 2H), 1.15 (d, J=6.9 Hz, 3H), 0.66 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 370 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 5 hours
  3. filtrationfiltered through Celite®, with THF washings
  4. concentrationconcentrated
  5. custompurified by flash chromatography on silica gel
  6. washeluting with 50% ethyl acetate/heptane to 100% ethyl acetate

Sources & evidence

ORD record
ord-d528da20f74f40ce9dda81aa6873de24
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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