Potassium Phosphate, Tribasic → 4-(3,6-dihydro-2H-pyran-4-yl)-N-methylaniline

HRID 63661

Reaction equation

HRID 63661 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH2:10][CH2:11][O:12][CH2:13][CH:14]=2)O1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:54]1[CH:61]=[CH:60][C:57]([NH:58][CH3:59])=[CH:56][CH:55]=1>C1(C)C=CC=CC=1.O.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]>[O:12]1[CH2:13][CH:14]=[C:9]([C:54]2[CH:61]=[CH:60][C:57]([NH:58][CH3:59])=[CH:56][CH:55]=2)[CH2:10][CH2:11]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2757052Benzenamine, 4-bromo-N-methyl-HCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 1185975924-(3,6-dihydro-2H-pyran-4-yl)-N-methylanilineYield 76.5%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 22272177Toluene waterSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (800 mg, 3.8 mmol), S-Phos (160 mg, 0.38 mmol), Pd2(dba)3 (72 mg, 0.08 mmol), and K3PO4 (96 mg, 3.8 mmol) in toluene/H2O (100 mL/20 mL) was added 4-bromo-N-methylaniline (712 mg, 3.84 mmol) under N2. After stirring at 115° C. overnight, the reaction mixture was filtered and concentrated. The residue was purified by silica gel chromatography (PE:EtOAc=10:1) to give 550 mg (76%) of the title compound as a yellow solid. [M+H] Calc'd for C12H15NO, 190. Found, 190.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (PE:EtOAc=10:1)

Sources & evidence

ORD record
ord-20377d5f5b7543efa46333e58ed73772
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Linked notes

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