Potassium Carbonate → HCID 22667745, compound

HRID 844127Notes

Reaction equation

HRID 844127 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](B(O)O)[CH:12]=2)[NH:7][C:6](=[O:17])[CH2:5]1)([CH3:3])[CH3:2].Br[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.C(O)C.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>[Cl:26][C:21]1[CH:20]=[C:19]([C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6](=[O:17])[CH2:5][N:4]3[CH:1]([CH3:3])[CH3:2])[CH:24]=[CH:23][C:22]=1[F:25]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 35430654-Bromo-2-chloro-1-fluorobenzeneHCID 22667737HCID 22667737, compound

Product 1

HCID 22667745HCID 22667745, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (3,4-dihydro-4-isopropyl-2-oxoquinoxalin-6-yl)boronic acid (2.4 g, 10 mmol), 4-bromo-2-chlorofluorobenzene (2 g, 10 mmol), potassium carbonate (4 g, 30 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.46 g, 0.4 mmol) in dimethoxyethane (100 ml), ethanol (25 ml) and water (25 mol) was heated to reflux for 6 hrs. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate (3×). The combined organic layers were washed with water, then brine, dried (MgSO4) and evaporated to obtain crude product (2.9 g, 91%). Recrystallization from EtOAc/hexane afforded the title compound, mp 208-213° C.: 1H-NMR (DMSO-d6) δ1.16 (d, J=6.59 Hz, 6H), 3.56 (s, 2H), 4.22 (septet, J=6.59 Hz, 1H), 6.86 (d, J=7.91 Hz, 1H), 6.96 (dd, J=7.91, 1.76 Hz, 1H), 7.01 (d, J=1.76 Hz, 1H), 7.43 (t, J=9.01 Hz, 1H), 7.61 (m, 1H), 7.82 (dd, J=7.14, 2.31 Hz, 1H), 10.47 (s, 1H). MS (EI) m/z 318 [M]++1 chlorine.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 hrs
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic layers were washed with water
  5. dry with materialbrine, dried (MgSO4)
  6. customevaporated
  7. customto obtain crude product (2.9 g, 91%)
  8. customRecrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-989c4644c1a44b6987066fdae47c7c90
Source dataset
uspto-grants-2002_04
Patent number
US06380235B1

Reaction notes

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