Phenylboronic Acid → 3-Phenyl-5,6,8,9-tetrahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester

HRID 239165Notes

Reaction equation

[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([O:14][C:15]([N:17]1[CH2:23][CH2:22][C:21]2[N:24]=[N:25][C:26](Cl)=[CH:27][C:20]=2[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>O1CCOCC1.O>[C:10]([O:14][C:15]([N:17]1[CH2:23][CH2:22][C:21]2[N:24]=[N:25][C:26]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:27][C:20]=2[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

Conditions

Temperature: 90 °C

Procedure

5 g phenylboronic acid in 30 mL dioxane was added to 3.2 g 3-chloro-5,6,8,9-tetrahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester and 388 mg (1,1′-bis(diphenyl-phosphinoferrocene)palladium(II)dichloride in 50 mL dioxane under argon. The reaction was stirred at 90° C. over night. The mixture was cooled to RT diluted with water and extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydroxide and brine. The solvent was removed and the precipitate was purified by column chromatographie to yielded 5.5 g of the desired product. (M+H)+=325

Workup

temperatureThe mixture was cooled to RT
extractionextracted with ethyl acetate
washThe organic layer was washed with aqueous sodium hydroxide and brine
customThe solvent was removed
customthe precipitate was purified by column chromatographie

Sources & evidence

ORD record: ord-7798f45972a64ffd9a68ab0f8087785b
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642774B2

Reaction notes

Loading…