Potassium Carbonate → 6-(3-fluorophenyl)-4,4-dimethyl-3,4-dihydroquinoline-2(1H)-one

HRID 2120750Notes

Reaction equation

HRID 2120750 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[CH2:16][C:15]2([CH3:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.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>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17](=[O:22])[CH2:16][C:15]3([CH3:24])[CH3:23])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 107295896-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 99433246-(3-fluorophenyl)-4,4-dimethyl-3,4-dihydroquinoline-2(1H)-one

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Prepared by coupling 3-fluorophenylboronic acid with an equivalent amount of 6-bromo-4,4-dimethyl-3,4-dihydo-1H-quinolin-2-one using a catalytic amount of tetrakis(triphenylphosphine)palladium (0) with overnight refluxing in toluene containing an equivalent amount of potassium carbonate dissolved in water. Work up in the usual manner followed by recrystallization from ethanol gave a gray solid: mp 190-192° C. 1H-NMR (DMSO-d6) δ 10.27 (s, 1H), 7.57 (s, 1H), 7.50 (r, 4H), 7.15 (m, 1H), 6.95 (d, 1H J=8.2 Hz), 2.39 (s, 2H), 1.29 (s, 6H); MS (APCI (−)) m/z 268 [M−H]− Anal. Calc. For C17H16FNO 0.25H2O: C, 74.57, H, 6.07, N, 5.12. Found: C, 74.86, H, 5.97, N 5.06.

Workup

  1. customPrepared
  2. customwith overnight
  3. customfollowed by recrystallization from ethanol
  4. customgave a gray solid

Sources & evidence

ORD record
ord-460276a5092a4f4f86425092b02ae437
Source dataset
uspto-grants-2004_02
Patent number
US06693103B2

Reaction notes

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