Hexane → HCID 18507143, compound

HRID 1633548Notes

Reaction equation

CCCCCC.[H-].[Na+].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH2:17][C:18]#[N:19])[CH:14]=[CH:15][CH:16]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][N:22]=1>CN(C=O)C.CCOCC.O>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([CH:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH3:9])[CH:12]=2)[C:18]#[N:19])=[N:22][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of hexane washed 60% sodium hydride (2.65, 66.0 mmol) in DMF (30 mL) at 0° C. was added 3-methoxyphenyl acetonitrile (8.0 g, 54.3 mmol). The reaction mixture was stirred at 0° C. for 30 min. A solution of 2,5-dibromopyridine (15.45 g, 65.2 mmol) in DMF(20 mL) was added and the reaction was stirred at room temperature for 20 min and at 50° C. for 30 min. To the reaction mixture was added H2O (20 mL) and Et2O (200 mL). The organic layer was washed with brine (5×50 mL), dried over Na2SO4 and concentrated. Purification by flash chromatography with hexanes/EtOAc (10:1) afforded 10.6 g of (5-Bromo-pyridin-2-yl)-(3-methoxy-phenyl)-acetonitrile. 1HNMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 7.80 (dd, 1H), 7.27 (comp, 2H), 6.98 (d, 1H), 6.87 (s, 1H), 6.84 (m, 1H), 5.28 (s, 1H), 5.23 (s, 3H); MS (M+1) 303.0, 305.0.

Workup

stirringthe reaction was stirred at room temperature for 20 min and at 50° C. for 30 min
washThe organic layer was washed with brine (5×50 mL)
dry with materialdried over Na2SO4
concentrationconcentrated
customPurification by flash chromatography with hexanes/EtOAc (10:1)

Sources & evidence

ORD record: ord-7b61c745a29d48b5b6353e6a6c4d342f
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503905B1

Reaction notes

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