Sodium Carbonate → 2-Chloro-9-(4-fluorophenyl)-3-phenylpyrimido[1,2-b]indazole

HRID 877060Notes

Reaction equation

HRID 877060 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[C:5]3[N:14]=[C:13]([Cl:15])[C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:11][N:6]3[N:7]=2)[CH:3]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[Cl:15][C:13]1[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][N:6]2[N:7]=[C:8]3[C:4]([CH:3]=[C:2]([C:26]4[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=4)[CH:10]=[CH:9]3)=[C:5]2[N:14]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 867025279-Bromo-2-chloro-3-phenylpyrimido[1,2-b]indazole

Product 1

HCID 867025352-Chloro-9-(4-fluorophenyl)-3-phenylpyrimido[1,2-b]indazole

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

300 mg (0.84 mmol) 9-Bromo-2-chloro-3-phenylpyrimido[1,2-b]indazole, (intermediate example Int-1-2), 128.7 mg (0.92 mmol) (4-fluorophenyl)boronic acid, 68.3 mg (0.084 mmol) bis(diphenylphosphino)ferrocenedichloropalladium(II) and 1.5 mL aqueous sodium carbonate solution (10%) in 10 mL dimethoxyethane were heated in the microwave oven for 45′ at 110° C. The reaction mixture was poured on water/dichloromethane and stirred vigorously for 30′. The organic phase was separated and washed twice with brine. After drying and filtration the solvent was evaporated and the residue (194 mg), a mixture (according to UPLC/MS) of the title compound, the regioisomer 9-bromo-2-(4-fluorophenyl)-3-phenyl-pyrimido[1,2-b]indazole and the bisproduct 2,9-bis-(4-fluorophenyl)-3-phenyl-pyrimido[1,2-b]indazole, was used in the next step without further purification.

Workup

  1. customat 110° C
  2. additionThe reaction mixture was poured on water/dichloromethane
  3. customThe organic phase was separated
  4. washwashed twice with brine
  5. customAfter drying
  6. filtrationfiltration the solvent
  7. customwas evaporated
  8. customthe residue (194 mg), a mixture (according to UPLC/MS) of the title compound, the regioisomer 9-bromo-2-(4-fluorophenyl)-3-phenyl-pyrimido[1,2-b]indazole and the bisproduct 2,9-bis-(4-fluorophenyl)-3-phenyl-pyrimido[1,2-b]indazole, was used in the next step without further purification

Sources & evidence

ORD record
ord-fe5918173f094a3c8f306c26b5f61d67
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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