Potassium Carbonate → HCID 86585689, compound

HRID 2230046Notes

Reaction equation

HRID 2230046 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:15])[CH:8]3[CH2:14][CH2:13][CH2:12][N:9]32)=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.C(O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:16][C:17]1[CH:22]=[C:21]([CH:12]2[N:9]3[C:10]4[C:5]([NH:6][C:7](=[O:15])[CH:8]3[CH2:14][CH2:13]2)=[CH:4][CH:3]=[CH:2][CH:11]=4)[CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 22667747HCID 22667747, compound

Product 1

HCID 86585689HCID 86585689, compoundYield 7%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 8-bromo-1,2,3,3a-tetrahydro-5H-pyrrolo(1,2-a)quinoxalin-4-one (2.7 g, 10 mmol), 3-chlorophenyl boronic acid (1.6 g, 10 mmol), potassium carbonate (4 g, 30 mmol), and tetrakis(triphenylphosphine) palladium(0) (0.5 g, 0.43 mmol) in dimethoxyethane (100 ml), ethanol (25 ml), and water (25 ml) was heated to reflux for 6 hours. After cooling to room temperature, the mixture was diluted with water and extracted with EtOAc (3×60 mL). The combined organic extracts were washed with water, then brine, dried (MgSO4) and evaporated. The crude product (1.5 g) was recrystallized from EtOAc/hexane to afford the title compound (0.2 g, 7%): mp 210° C.; MS (+APCI) m/z 299 ((M+H)+).

Workup

  1. temperatureto reflux for 6 hours
  2. extractionextracted with EtOAc (3×60 mL)
  3. washThe combined organic extracts were washed with water
  4. dry with materialbrine, dried (MgSO4)
  5. customevaporated
  6. customThe crude product (1.5 g) was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-00cd57bf9d3f42989dff4990e7e9ec49
Source dataset
uspto-grants-2002_07
Patent number
US06423699B1

Reaction notes

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