Water → HCID 70816639, compound

HRID 576677Notes

Reaction equation

HRID 576677 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[CH:24]=[C:23](Cl)[N:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].O>C(COC)OC>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[CH:24]=[C:23]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[O:27][CH3:26])[N:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 86672047HCID 86672047, compound

Product 1

HCID 70816639HCID 70816639, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

235 mg (1H-Benzoimidazol-2-yl)-[4-(6-chloro-pyrimidin-4-ylamino)-benzyl]-amine (prepared in Example 86) (0.70 mmol) was suspended in 30 cm3 dimethoxyethane and the flask was filled with argon properly. 58 mg Tetrakis(thriphenylphosphine) palladium[0] (0.05 mmol) was added and the mixture was stirred at room temperature for 30 minutes. Then 152 mg 2-methoxyphenyl-boronic acid (1 mmol), 318 mg anhydrous Na2CO3 (3 mmol) and 6 ml water were added. The mixture was refluxed overnight while slow argon flow was being applied. The reaction mixture was poured to 80 cm3 1M NaH2PO4 solution and it was extracted three times with 50-50 cm3 of ethyl-acetate. The combined organic layer was washed with brine, dried over MgSO4, decolorized with activated carbon and evaporated to dryness. The residual solid was recrystallized from minimal amount of acetonitrile and air-dried to give the desired product (125 mg, 44% yield). For analitical results and compound identification see Table 1.

Workup

  1. additionthe flask was filled with argon properly
  2. temperatureThe mixture was refluxed overnight while slow argon flow
  3. extractionwas extracted three times with 50-50 cm3 of ethyl-acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customThe residual solid was recrystallized from minimal amount of acetonitrile
  8. customair-dried

Sources & evidence

ORD record
ord-15a0a44bff20417da22da31576742036
Source dataset
uspto-grants-2015_05
Patent number
US09040529B2

Reaction notes

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