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

HRID 277875Notes

Reaction equation

HRID 277875 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-dihydro-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 (m, 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 0.25 H2O: 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-05b9b20ce0d14d508264f927603049c1
Source dataset
uspto-grants-2002_03
Patent number
US06358948B1

Reaction notes

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