Ethanol → 3-Methyl-7-(4-fluorophenylsulfonyl)-9-phenyl-1,2,4,5-tetrahydro-3-benzazepine

HRID 1784424Notes

Reaction equation

HRID 1784424 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][C:6]2[C:9](I)=[CH:10][C:11]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])=[CH:12][C:5]=2[CH2:4][CH2:3]1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>C1(C)C=CC=CC=1.O>[CH3:1][N:2]1[CH2:8][CH2:7][C:6]2[C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:10][C:11]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])=[CH:12][C:5]=2[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 688312513-Methyl-7-(4-fluorophenylsulfonyl)-9-iodo-1,2,4,5-tetrahydro-3-benzazepine

Product 1

HCID 575924903-Methyl-7-(4-fluorophenylsulfonyl)-9-phenyl-1,2,4,5-tetrahydro-3-benzazepineYield 75.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-methyl-7-(4fluorophenylsulfonyl)-9-iodo-1,2,4,5-tetrahydro-3-benzazepine (0.9 g, 2 mmol), phenylboronic acid (0.4 g, 3 mmol), potassium carbonate (1.6 g, 12 mmol), ethanol (6 ml), water (6 ml), and toluene (25 ml) was degassed, then tetrakis(triphenylphosphine)palladium (0) (100 mg) was added and the mixture heated at 60° C. for 18 h. After cooling the mixture was poured into water (50 ml) and extracted with more ethyl acetate (50 ml). The resulting organic layer washed with brine (100 ml), dried (MgSO4), and evaporated. Isolation using an SCX column and subsequent chromatography on silica eluting with 0 to 10% methanol in dichloromethane containing 0.1M ammonia, gave the title compound as a white foam (0.6 g). 1H NMR δ (d6-DMSO) 2.2 (3H, s), 2.5 (4H, m), 2.8 (2H, m), 3.1 (2H, m), 7.2 (2H, m), 7.4 (5H, m), 7.6 (1H, s), 7.8 (1H, s), and 8.1 (2H, m).

Workup

  1. customwas degassed
  2. additiontetrakis(triphenylphosphine)palladium (0) (100 mg) was added
  3. temperatureAfter cooling the mixture
  4. additionwas poured into water (50 ml)
  5. extractionextracted with more ethyl acetate (50 ml)
  6. washThe resulting organic layer washed with brine (100 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-77b6ebea9ae740e98152eae62cd359e5
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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