Sodium Carbonate → HCID 178518679, compound

HRID 2358264Notes

Reaction equation

HRID 2358264 reaction equation
Br[C:2]1[CH:27]=[CH:26][C:5]2=[C:6]3[N:17]=[C:16]([C:18]4[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:25])[NH:15][C:7]3=[C:8]3[C:13]([C:12](=[O:14])[NH:11][CH:10]=[CH:9]3)=[C:4]2[CH:3]=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][N:30]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1>[Cl:25][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([F:24])[C:18]=1[C:16]1[NH:15][C:7]2=[C:8]3[C:13](=[C:4]4[CH:3]=[C:2]([C:32]5[CH:31]=[N:30][C:29]([Cl:28])=[CH:34][CH:33]=5)[CH:27]=[CH:26][C:5]4=[C:6]2[N:17]=1)[C:12](=[O:14])[NH:11][CH:10]=[CH:9]3

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27947192-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 178518678HCID 178518678, compound

Product 1

HCID 178518679HCID 178518679, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

9-Bromo-2-(2-chloro-6-fluorophenyl)-3,6-dihydro-7H-benzo[h]imidazo[4,5-f]isoquinolin-7-one (500 mg, 1.130 mmol) was dissolved in ethanol (15 ml) and toluene (15.00 ml). (Dichlorobis)palladiumtriphenylphosphine (79 mg, 0.113 mmol), 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (298 mg, 1.242 mmol) and Na2CO3 (2 M, 1.135 mL) were added and argon was bubbled through the solution for several minutes. The solution was heated at 80° C. for 2 hours. The reaction mixture was cooled to ambient temperature and diluted with ethyl acetate and water. The organic layer was separated, dried over magnesium sulftate, filtered and concentrated. The crude residue was purified via a chiral AD column which afforded the title compound. 1H NMR (500 MHz, CD3OD, δH) 10.68 (s, 1 H), 8.56 (d, 1 H, J=1.8 Hz), 8.30 (dd, 1 H, J=8.4, 3.0 Hz), 8.04 (dd, 1 H) J=9.0, 1.8 Hz), 7.68-7.64 (m, 1 H), 7.63-7.60 (m, 2 H), 7.54 (d, 1 H, J=8.4 Hz), 7.38 (td, 1 H, J =9, 1.2 Hz): [M+1]+ 475.

Workup

  1. customargon was bubbled through the solution for several minutes
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. additiondiluted with ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulftate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified via a chiral AD column which

Sources & evidence

ORD record
ord-44caa06cdaf24ae5b520c32b7384476f
Source dataset
uspto-grants-2010_07
Patent number
US07763634B2

Reaction notes

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