Potassium Phosphate, Tribasic → HCID 67500563, compound

HRID 921582Notes

Reaction equation

HRID 921582 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[C:15]2=[N:16][CH:17]=[CH:18][C:19]([N:20]3[CH:24]=[C:23]([C:25]4[CH:26]=[N:27][N:28]([CH3:30])[CH:29]=4)[N:22]=[CH:21]3)=[C:14]2[C:13]([C:31]([F:34])([F:33])[F:32])=[N:12]1)[C:5]([NH2:7])=[O:6].[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(Cl)(Cl)Cl>[CH3:30][N:28]1[CH:29]=[C:25]([C:23]2[N:22]=[CH:21][N:20]([C:19]3[CH:18]=[CH:17][N:16]=[C:15]4[N:11]([C:10]5[C:2]([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)=[CH:3][C:4]([C:5]([NH2:7])=[O:6])=[CH:8][CH:9]=5)[N:12]=[C:13]([C:31]([F:32])([F:33])[F:34])[C:14]=34)[CH:24]=2)[CH:26]=[N:27]1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 75806TricyclohexylphosphineHCID 67500180HCID 67500180, compound

Product 1

HCID 67500563HCID 67500563, compoundYield 6.1%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

Compound (153) (0.030 g), phenylboronic acid (0.014 g), palladium acetate (0.001 g), tricyclohexylphosphine (0.004 g), and potassium phosphate (0.050 g) were dissolved in toluene (0.5 mL) and water (0.025 mL), followed by stirring using microwaves at 130° C. for 10 min. The reaction solution was distributed between chloroform and water, and the organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain compound (172) (0.002 g, 6%) as a white solid.

Workup

  1. customat 130° C.
  2. customfor 10 min
  3. washthe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled away
  6. customthe residue was purified by neutral silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-f05b4259f5a94150835123203558bdc2
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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