Borane;tetrahydrofuran → 4-[(Indolizin-3-yl)methyl]benzonitrile

HRID 982695Notes

Reaction equation

HRID 982695 reaction equation
[CH:1]1[CH:2]=[C:3]([C:10]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)=O)[N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]2.B.C1COCC1>CO>[CH:1]1[CH:2]=[C:3]([CH2:10][C:12]2[CH:13]=[CH:14][C:15]([C:16]#[N:17])=[CH:18][CH:19]=2)[N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 102639353-(4-cyanobenzoyl)indolizine

Product 1

HCID 225632004-[(Indolizin-3-yl)methyl]benzonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To 4-(indolizine-3-carbonyl)-benzonitrile (24 g, 100 mmol) CH3CN (600 ml) solution containing MeOH (9 ml) was added BH3-THF (1M, 480 ml). The resulting mixture was stirred at 50° C. for 1 hr. The reaction was quenched with water (200 ml), and extracted with EtOAc (700 ml), and washed with water (300 ml×3). The organic layer was evaporated under reduced pressure, and the residue was dissolved in ether (or EtOAc) (400 ml), diluted with hexanes (100 ml) and filtered with celite to give 4-indolizin-3-ylmethyl-benzonitrile (15.6 g, 92% purity by HPLC). This product was used directly for the next step. δ (ppm) 8.54 (m, 1H); 7.59 (m, 3H); 7.39 (m, 2H); 7.31 (m, 1H); 7.19 (m, 1H); 3.01 (t, J=6.9 Hz, 2H); 2.75 (t, J=6.9 Hz, 2H). ESMS calcd. (C16H12N2): 232.1. found: 233.1 (M+H)+.

Workup

  1. customThe reaction was quenched with water (200 ml)
  2. extractionextracted with EtOAc (700 ml)
  3. washwashed with water (300 ml×3)
  4. customThe organic layer was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in ether (or EtOAc) (400 ml)
  6. additiondiluted with hexanes (100 ml)
  7. filtrationfiltered with celite

Sources & evidence

ORD record
ord-6977797d95e7486283f4123fda4f9abf
Source dataset
uspto-grants-2005_03
Patent number
US06861436B2

Reaction notes

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