Triethylamine → HCID 136038172, compound

HRID 1619291Notes

Reaction equation

HRID 1619291 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)#[CH:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC>O.CC([O-])=O.CC([O-])=O.[Pd+2].[Cu]I.CN(C=O)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]#[C:14][C:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]3)=[CH:4][CH:3]=2)=[CH:16][CH:17]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 5226271-Ethynyl-4-fluorobenzeneHCID 1355556127-Bromo-3,4-dihydroquinazolin-4-one

Product 1

HCID 136038172HCID 136038172, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A flask was charged with 7-bromoquinazolin-4(3H)-one (60 mg, 0.27 mmol, 1 equiv), 1-ethynyl-4-fluorobenzene (81 mg, 0.675 mmol, 2.5 equiv), Pd(OAc)2 (12.2 mg, 0.054 mmol, 0.2 equiv), PPh3 (63.7 mg, 0.24 mmol, 0.9 equiv), CuI (10.3 mg, 0.054 mmol, 0.2 equiv), Et3N (0.3 mL) and DMF (6 mL). A vacuum was applied and the reaction mixture was back filled with nitrogen three times. The mixture was stirred at 70° C. for 3.5 hours. After it was cooled to room temperature, the reaction mixture was diluted with H2O and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, then concentrated under reduced pressure and purified by column chromatography to give the desired product. MS (ESI): 265 (MH+); 1H NMR (300 MHz, DMSO-d6) δ 12.38-12.33 (m, 1H), 8.13 (s, 2H), 7.81 (s, 1H), 7.69-7.54 (m, 3H), 7.39-7.29 (m, 2H).

Workup

  1. additionthe reaction mixture was back filled with nitrogen three times
  2. temperatureAfter it was cooled to room temperature
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-f15505fa00684a4596b5f47f3098917b
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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