Potassium Carbonate → HCID 58269374, compound

HRID 2046482Notes

Reaction equation

HRID 2046482 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][CH:6]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3Br)[CH2:5][C:4]=2[N:3]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23](B(O)O)[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][CH:6]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[C:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)[CH2:5][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 58269415HCID 58269415, compound

Product 1

HCID 58269374HCID 58269374, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To a microwave vessel was added 2-amino-7-(2-bromo-4-fluoro-phenyl)-7,8-dihydro-6H-quinazolin-5-one (30 mg, 0.089 mmol), example 2/i stage 2, pyridine-3-boronic acid (22 mg, 0.11 mmol), potassium carbonate (51 mg, 0.22 mmol) and tetrakis(triphenylphosphine)palladium (9 mg, 5 mol %), in a 2:1 mixture of ethanol:toluene (1 ml) and the suspension thoroughly degassed. The reaction mixture was then heated in a CEM microwave at 300 W, 150° C. with a 5 min ramp time and a hold time of 30 min. On completion of the reaction the solution was filtered through celite and then the cake further washed with fresh methanol. The combined washings were evaporated to give a pale yellow residue which was triturated with fresh diethyl ether and the desired product removed by filtration as a pale yellow solid.

Workup

  1. customtoluene (1 ml) and the suspension thoroughly degassed
  2. customa hold time of 30 min
  3. customOn completion of the reaction the solution
  4. filtrationwas filtered through celite
  5. washthe cake further washed with fresh methanol
  6. customThe combined washings were evaporated
  7. customto give a pale yellow residue which
  8. customwas triturated with fresh diethyl ether
  9. customthe desired product removed by filtration as a pale yellow solid

Sources & evidence

ORD record
ord-cdc945e5e0354f96b64102914f62874e
Source dataset
uspto-grants-2013_11
Patent number
US08592430B2

Reaction notes

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