Cesium carbonate → HCID 59596249, compound

HRID 2264772Notes

Reaction equation

HRID 2264772 reaction equation
C(O)(=O)C.Br[C:6]1[CH:7]=[C:8]([C:12]2([C:22]3[CH:23]=[N:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=3)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([NH2:21])=[N:13]2)[CH:9]=[CH:10][CH:11]=1.[N:32]1[CH:37]=[C:36](B(O)O)[CH:35]=[N:34][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.C(O)C.O>[N:32]1[CH:37]=[C:36]([C:6]2[CH:7]=[C:8]([C:12]3([C:22]4[CH:23]=[N:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=4)[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]([NH2:21])=[N:13]3)[CH:9]=[CH:10][CH:11]=2)[CH:35]=[N:34][CH:33]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 67273396HCID 67273396, compound

Product 1

HCID 59596249HCID 59596249, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
130 °C

Procedure

1-(3-Bromophenyl)-1-[6-(trifluoromethyl)pyridin-3-yl]-1H-isoindol-3-amine acetate (Example 52, 0.046 g, 0.09 mmol), pyrimidine-5-boronic acid (0.023 g, 0.186 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct (0.004 g, 0.0046 mmol) and cesium carbonate (0.092 g, 0.284 mmol) were dissolved in 1,2-dimethoxy ethane:ethanol:water (6:3:1, 2 mL) and heated to 130° C. for 20 minutes in a microwave oven. Additional [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct (0.004 g, 0.0046 mmol) was added and the resulting mixture was heated to 130° C. for additional 20 minutes. After cooled to ambient temperature the mixture was filtered and purified by preparative HPLC to give 0.011 g (26% yield) of the title compound. 1H NMR (MeOD) δ 9.12 (s, 1 H), 9.02-8.95 (m, 2 H), 8.64 (d, J=2.02 Hz, 1 H), 8.06-7.92 (m, 2 H), 7.80 (dd, J=7.96, 2.40 Hz, 2 H), 7.76-7.69 (m, 2 H), 7.68-7.61 (m, 2 H), 7.57 (t, J=7.83 Hz, 1 H), 7.49-7.41 (m, 1 H), 1.94 (s, 2 H); MS (ES) m/z 430 [M−H]−, m/z 432 [M+H]+.

Workup

  1. temperaturethe resulting mixture was heated to 130° C. for additional 20 minutes
  2. temperatureAfter cooled to ambient temperature the mixture
  3. filtrationwas filtered
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-2d1771fbbef94e629dda2e6f5f13067c
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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