Acetonitrile → 4-[(Indolizin-3-yl)methyl]benzonitrile

HRID 982692Notes

Reaction equation

HRID 982692 reaction equation
C([BH3-])#N.[Na+].C(#N)C.[C:8]([C:10]1[CH:26]=[CH:25][C:13]([C:14]([C:16]2[N:24]3[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]3)=[CH:18][CH:17]=2)=O)=[CH:12][CH:11]=1)#[N:9].C(OCC)(=O)C>CCCCCC>[C:8]([C:10]1[CH:11]=[CH:12][C:13]([CH2:14][C:16]2[N:24]3[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]3)=[CH:18][CH:17]=2)=[CH:25][CH:26]=1)#[N:9]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 5003444Sodium cyanoborohydrideHCID 102639353-(4-cyanobenzoyl)indolizine

Product 1

HCID 225632004-[(Indolizin-3-yl)methyl]benzonitrileYield 56.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Sodium cyanoborohydride (0.32 grams, 5.06 mmol) was added in portions to an acetonitrile (15 mL) solution of 3-(4-cyanobenzoyl)indolizine (13) (0.19 grams, 0.84 mmol) and chlorotrimethylsilanen (0.65 mL, 5.06 mmol) cooled in an ice-bath. The reaction mixture was stirred at room temperature for 4 hours. It was then quenched with aqueous sodium bicarbonate solution, extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with water, dried over sodium sulfate and concentrated in vacuo to give an oily residue, which was applied to the flash column chromatography using 10% ethyl acetate in hexane (Rf 0.3) to afford 3-(4-cyanobenzyl)indolizine (14) (0.11 grams, 56% yield). 1H NMR (CDCl3) δ 4.09 (s, 2H), 6.36 (m, 2H), 6.56 (m, 2H), 7.15 (d, J=8.4, 2H), 7.32 (d, J=9.3, 1H), 7.45 (m, 3H). ESMS calcd (C16H12N2): 232.1. found: 233.1 (M+H)+.

Workup

  1. temperaturecooled in an ice-bath
  2. customIt was then quenched with aqueous sodium bicarbonate solution
  3. extractionextracted with ethyl acetate (3×25 mL)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an oily residue, which

Sources & evidence

ORD record
ord-56841c17abce4e9f9d2a63f2a99e8633
Source dataset
uspto-grants-2005_03
Patent number
US06861436B2

Reaction notes

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