3-Bromopyridine → HCID 86611795, compound

HRID 1695577Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([NH:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:6].C([O-])(=O)C.[K+].Br[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][CH:8]1[NH:7][C:5](=[O:6])[C:4]1[CH:17]=[CH:18][CH:19]=[C:2]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

100 mg of 3-bromo-N-indan-2-yl-benzamide, 88 mg bis-(pinacolato)-dibor, 93 mg potassium acetate and 48 mg PdCl(dppf) were dissolved in 6 ml DMF and stirred at 80° C. for 2 h. The solution was cooled to ambient temperature and 100 mg of 3-bromo-pyridine added. Then, further 24 mg of PdCl(dppf) were added and the mixture stirred at 80° C. for 3.5 h. The mixture was cooled to ambient temperature and diluted with 20 ml ethyl acetate. The crude mixture was washed three times with 5 ml of a saturated aqueous solution of Na2CO3 each and dried over MgSO4. The solvents were removed under reduced pressure and the residue purified by chromatography on silica gel using MTB. Yield 60 mg of a viscous oil. Rf (MTB)=0.2.

Workup

temperatureThe solution was cooled to ambient temperature
stirringthe mixture stirred at 80° C. for 3.5 h
temperatureThe mixture was cooled to ambient temperature
washThe crude mixture was washed three times with 5 ml of a saturated aqueous solution of Na2CO3 each and
dry with materialdried over MgSO4
customThe solvents were removed under reduced pressure
customthe residue purified by chromatography on silica gel using MTB

Sources & evidence

ORD record: ord-1e7e544300d24d0798276c7d875bea7e
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163751B2

Reaction notes

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