Sodium Carbonate → HCID 54403989, compound

HRID 1351845Notes

Reaction equation

HRID 1351845 reaction equation
[CH2:1]([N:8]([CH:16]1[CH2:22][CH2:21][CH2:20][C:19]2[CH:23]=[CH:24][C:25](OC(F)(F)F)=[CH:26][C:18]=2[CH2:17]1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6]C=[CH:4][CH:3]=1.[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[C:41](=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH:16]1[CH2:22][CH2:21][CH2:20][C:19]2[CH:23]=[CH:24][C:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:26][C:18]=2[CH2:17]1)[C:2]1[CH:3]=[CH:4][CH:41]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 18007406HCID 18007406, compound

Product 1

HCID 54403989HCID 54403989, compoundYield 115.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of N-benzyl-N-tert-butoxycarbonyl-(3-trifluoromethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (500 mg) in toluene (6 ml) and water (2 ml) were added phenylboronic acid (122 mg), sodium carbonate (210 mg) and tetrakis(triphenylphosphine)palladium(0) (35 mg), and the mixture was stirred at 80° C. for 3.5 hours. The resulting mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=30:1 to 20:1) to give N-benzyl-N-(3-phenyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-tert-butoxycarbonylamine (494 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=30:1 to 20:1)

Sources & evidence

ORD record
ord-286b185e23e544c0973b497ff04f1bcd
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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