1-Bromo-3-chloropropane → HCID 18507150, compound

HRID 1355575Notes

Reaction equation

CCCCCC.[H-].[Na+].[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[C:17]#[N:18])=[N:14][CH:15]=1.Br[CH2:28][CH2:29][CH2:30][Cl:31]>CN(C=O)C.CCOCC>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)([CH2:28][CH2:29][CH2:30][Cl:31])[C:17]#[N:18])=[N:14][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of hexane washed 60% sodium hydride (0.35 g, 8.6 mmol) in DMF (2 mL) at 0° C. was added a solution of (5-bromo-pyridin-2-yl)-(3-methoxy-phenyl)-acetonitrile (1.75 g, 5.76 mmol) in DMF (5 mL). The reaction mixture was stirred at 0° C. for 30 min and at room temperature for 1 h. 1-bromo-3-chloropropane (0.69 mL, 6.91 mmol) was added and the mixture was stirred at room temperature for 4 h. To the reaction mixture was added H20 (5 mL) and Et2O and the organic layer was washed with brine (5x5 mL), dried over Na2SO4 and concentrated. Purification by flash chromatography with hexanes/EtOAc (10:1) yielded 1.81 9 of 2-(5-bromo-pyridin-2-yl)-5-chloro-2-(3-methoxy-phenyl)-pentanenitrile. 1HNMR (400 MHz, CDCl3) 6 8.65 (s, 1H), 7.76 (dd, 1H), 7.36 (d, 1h), 7.27-7.21 (m, 1H), 7.03 (d, 1H), 6.98 (s, 1H), 6.82 (dd,1H), 4.77 (s, 3H), 3.55 (t, 2H), 2.79-2.70 (comp, 1H), 2.62-2.52 (comp, 1H) 1.89-1.79 (comp, 2H); MS (M+1)378.8, 380.8.

Workup

stirringthe mixture was stirred at room temperature for 4 h
washthe organic layer was washed with brine (5x5 mL)
dry with materialdried over Na2SO4
concentrationconcentrated
customPurification by flash chromatography with hexanes/EtOAc (10:1)

Sources & evidence

ORD record: ord-e507a122be4d4c058bb7c0b5c3a078bc
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586431B1

Reaction notes

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