Tris(1,1-dimethylethyl)phosphine → HCID 135524916, compound

HRID 269492Notes

Reaction equation

HRID 269492 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[O:15][N:14]=[CH:13][C:12]=3[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=3[F:23])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[N:24]1[CH:29]=[C:28](B(O)O)[CH:27]=[N:26][CH:25]=1.C([O-])(O)=O.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>COCCOC.C(OCC)(=O)C.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]>[F:23][C:17]1[C:18]([F:22])=[CH:19][CH:20]=[CH:21][C:16]=1[C:12]1[CH:13]=[N:14][O:15][C:11]=1[C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:28]3[CH:29]=[N:24][CH:25]=[N:26][CH:27]=3)[CH:3]=2)[NH:8][CH:9]=1

Participants

8

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 516892Sodium BicarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 136066551HCID 136066551, compound

Product 1

HCID 135524916HCID 135524916, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-3-[4-(2,3-difluoro-phenyl)-isoxazol-5-yl]-1H-pyrrolo[2,3-b]pyridine (prepared by Method A, 50 mg, 0.13 mmol) and 5-pyrimidine boronic acid (33 mg, 0.27 mmol) in DME (1 mL) was added sat. NaHCO3 (1.2 M, 0.54 mL, 0.65 mmol) and tri-tert-butylphosphine (27 mg, 0.13 mmol). The suspension was stirred under N2 atmosphere while catalyst PdCl2(dppf) (5 mg, 0.006 mmol) was added. The reaction mixture was then heated at 80° C. for 5 h and diluted with ethyl acetate. The inorganic salt was removed by filtration, the filtrate was evaporated and purified by HPLC to afford the desired product as off-white solid (5.0 mg, 0.013 mmol, 10%).

Workup

  1. additionwas added
  2. customThe inorganic salt was removed by filtration
  3. customthe filtrate was evaporated
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-853e906c1af94bfbb0e8f1fe82b426fa
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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