Potassium Phosphate, Tribasic → HCID 58994477, compound

HRID 1190202Notes

Reaction equation

HRID 1190202 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1Br.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:49][C:50]1([CH3:65])[CH2:55][CH2:54][C:53](B2OC(C)(C)C(C)(C)O2)=[CH:52][CH2:51]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[C:53]1[CH2:54][CH2:55][C:50]([CH3:65])([CH3:49])[CH2:51][CH:52]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 15152811-(4-Amino-3-bromo-phenyl)-ethanoneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 231420132-(4,4-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 58994477HCID 58994477, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a slurry of 1-(4-amino-3-bromo-phenyl)-ethanone (20.5 g, 0.960 mol, as prepared in the previous step), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (3.94 g, 9.60 mmol), and K3PO4 (61.0 g, 0.280 mol) in 250 mL of toluene was added 2-(4,4-dimethyl-cyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (24.9 g, 0.100 mol) followed by Pd2(dba)3 (4.39 g, 4.80 mmol). The resultant mixture was heated to 100° C. with vigorous stirring. After 3 h, the reaction was filtered and concentrated in vacuo. Purification of the residue by column chromatography (20% EtOAc-hexane) afforded the title compound (15.0 g, 64%). Mass spectrum (ESI, m/z): Calcd. for C16H21NO, 244.1 (M+H). found 244.2.

Workup

  1. filtrationthe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. customPurification of the residue by column chromatography (20% EtOAc-hexane)

Sources & evidence

ORD record
ord-7e4567ea057b4ab4877644ac274adf37
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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