Sodium Cyanide → 3-[1-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)cyclopropyl]propionitrile

HRID 1683978

Reaction equation

HRID 1683978 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3([CH2:21][CH2:22]Br)[CH2:20][CH2:19]3)=[C:8]2[CH3:24])=[CH:4][CH:3]=1.[C-:27]#[N:28].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3([CH2:21][CH2:22][C:27]#[N:28])[CH2:19][CH2:20]3)=[C:8]2[CH3:24])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 190417002-[1-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)cyclopropyI]ethyl bromide

Product 1

HCID 190416303-[1-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)cyclopropyl]propionitrileYield 97.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a r.t. solution of bromide from Step 9 (166 mg, 0.35 mmol) in 4 mL DMF was added NaH2PO4H2O (138 mg, 1 mmol) followed by NaCN (49 mg, 1 mmol) and the resulting mixture was warmed to 75° C. for 2 h. After diluting with excess H2O, the mixture was extracted with Et2O. The organic layer was washed with brine, dried over MgSO4 and evaporated to provide 144 mg of the title compound.

Workup

  1. extractionthe mixture was extracted with Et2O
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-f4b9262926634c5a902bb0832d8115cc
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Linked notes

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