Sodium hydride → 4-(3-methyl-2-pyridin-3-yl-1H-indol-1-ylmethyl)-benzonitrile

HRID 1633129Notes

Reaction equation

HRID 1633129 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.[C:19]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1)#[N:20]>CN(C)C=O.C1CCCCC1>[C:19]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([CH3:3])=[C:5]2[C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:23][CH:22]=1)#[N:20]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 155913683-Methyl-2-(3-pyridyl)indole

Product 1

HCID 155913804-(3-methyl-2-pyridin-3-yl-1H-indol-1-ylmethyl)-benzonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8078CyclohexaneSolvent

Procedure

To a suspension of 2.9 g (0.06 mole) of 50% sodium hydride in mineral oil in 40 ml of dimethylformamide under nitrogen at 0°-5° is added dropwise over 20 minutes a solution of 10.4 g (0.05 mole) of 3-methyl-2-(3-pyridyl)indole in 60 ml of dimethylformamide. The reaction mixture is stirred for 0.5 hour at 0°-5° followed by dropwise addition of 9.8 g (0.05 mole) of p-cyanobenzyl bromide in 50 ml of dimethylformamide. After stirring at 0°-10° for 1 hour and at room temperature for 0.5 hour, the reaction mixture is poured into ice-water (600 ml). The resulting solid is collected, dried, washed with petroleum ether and redissolved in ether (500 ml). The ether solution is first washed with water, then with saturated sodium bicarbonate solution, dried over MgSO4, treated with charcoal and filtered. Evaporation of the ether extract to dryness yields a yellow solid. This product is slurried in hot cyclohexane and collected by filtration to give 1-(4-cyanobenzyl)-3-methyl-2-(3-pyridyl)indole, m.p. 127°-129°.

Workup

  1. stirringAfter stirring at 0°-10° for 1 hour and at room temperature for 0.5 hour
  2. customThe resulting solid is collected
  3. customdried
  4. washwashed with petroleum ether
  5. dissolutionredissolved in ether (500 ml)
  6. washThe ether solution is first washed with water
  7. dry with materialwith saturated sodium bicarbonate solution, dried over MgSO4
  8. additiontreated with charcoal
  9. filtrationfiltered
  10. customEvaporation of the ether
  11. extractionextract to dryness
  12. customyields a yellow solid
  13. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a653b37d05f046c0857c3a1442f27159
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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