Hexane → HCID 18507143, compound

HRID 1355574Notes

Reaction equation

HRID 1355574 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>[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

7

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 693532,5-DibromopyridineHCID 88310(3-Methoxyphenyl)acetonitrile

Product 1

HCID 18507143HCID 18507143, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

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 (15.45g, 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 H20 (20 mL) and Et2O (200 mL). The organic layer was washed with brine (5x50 mL), dried over Na2SO4 and concentrated. Purification by flash chromatography with hexanes/EtOAc (10:1) afforded 10.6 g of (5-Bromopyridin-2-yl)-(3-methoxy-phenyl)-acetonitrile. 1HNMR (400 MHz, CDCl3) 6 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

  1. stirringthe reaction was stirred at room temperature for 20 min and at 50° C. for 30 min
  2. washThe organic layer was washed with brine (5x50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash chromatography with hexanes/EtOAc (10:1)

Sources & evidence

ORD record
ord-c4458eb87a384630b49110ad22b088bb
Source dataset
uspto-grants-2003_07
Patent number
US06586431B1

Reaction notes

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