Phenylboronic Acid → HCID 21864727, compound

HRID 395316Notes

Reaction equation

HRID 395316 reaction equation
[CH2:1]([N:8]1[CH2:18][CH:17]2[CH2:19][CH:10]([C:11]3[CH:12]=[CH:13][CH:14]=[C:15](I)[C:16]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O)C.O>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]1[CH2:18][CH:17]2[CH2:19][CH:10]([C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:16]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 66827Phenylboronic AcidHCID 517044Potassium AcetateHCID 19096565Water ethanolHCID 21864742HCID 21864742, compound

Product 1

HCID 21864727HCID 21864727, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

(For a discussion, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.) 10-Benzyl-3-iodo-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene (375.3 mg, 1.0 mmol), potassium acetate (785 mg, 8.0 mmol) and phenyl boronic acid (183 mg, 1.5 mmol) were combined in 10/1 ethanol/H2O (5 mL). The mixture was degassed (3 vacuum/N2 cycles), treated with tetrakis(triphenylphosphine)palladium(0) (57.5 mg, 0.05 mmol) and warmed to 90° C. for 18 h. The reaction was cooled, diluted with H2O and extracted with Et2O (3×50 mL). The organic layer was washed with brine (50 mL), dried (MgSO4), filtered and concentrated to provide an oil (180 mg, 55%). (TLC 4% ethyl acetate/hexanes Rf 0.18). GCMS m/e 325 (M)+.

Workup

  1. customThe mixture was degassed (3 vacuum/N2 cycles)
  2. temperatureThe reaction was cooled
  3. extractionextracted with Et2O (3×50 mL)
  4. washThe organic layer was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-916110519e714dbfb7cf3f85d72842c4
Source dataset
uspto-grants-2003_08
Patent number
US06605610B1

Reaction notes

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