Potassium Carbonate → HCID 46206974, compound

HRID 1662245Notes

Reaction equation

HRID 1662245 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([O:26][CH3:27])[CH:21]=3)[C:17]3[C:12](=[C:13]([F:18])[CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:19])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[N:28]1[CH:33]=[C:32](B(O)O)[CH:31]=[N:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C=O)C>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[C:11]([NH2:19])=[N:10][C:9]2([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([C:32]2[CH:33]=[N:28][CH:29]=[N:30][CH:31]=2)[CH:3]=1)[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([O:26][CH3:27])[CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acid2×HCID 67431569HCID 67431569, compound

Product 1

HCID 46206974HCID 46206974, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

1-(3-Bromo-4-fluorophenyl)-4-fluoro-1-(2-methoxypyridin-4-yl)-1H-isoindol-3-amine (98.9 mg, 0.23 mmol), 5-pyrimidinylboronic acid (31.3 mg, 0.25 mmol), 1,1′-bis (diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (9.39 mg, 0.01 mmol), 2 M aqueous potassium carbonate (0.345 mL, 0.69 mmol) and DMF (2.0 mL) were put in a microwave vial and irradiated in a microwave oven at 110° C. for 20 min. Additional 5-pyrimidinylboronic acid (18.51 mg, 0.15 mmol) and [1,1′-bis (diphenylphosphino)ferrocene]palladium(II) chloride (9.39 mg, 0.01 mmol) were added and the resulting mixture was irradiated at 110° C. for 40 min. The resulting product mixture was filtered and purified by preparative-HPLC to give the title compound (38.9 mg, 39.4% yield).

Workup

  1. customirradiated in a microwave oven at 110° C. for 20 min
  2. customthe resulting mixture was irradiated at 110° C. for 40 min
  3. filtrationThe resulting product mixture was filtered
  4. custompurified by preparative-HPLC

Sources & evidence

ORD record
ord-f7a419451a8a4609a2047d8719335e41
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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