Dimethylformamide → HCID 68524610, compound

HRID 222475Notes

Reaction equation

HRID 222475 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].CN(C=O)C.Br[CH2:18][CH:19]1[CH2:21][CH2:20]1>>[CH:19]1([CH2:18][N:8]2[C:9]3[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=3)[CH:6]=[CH:7]2)[CH2:21][CH2:20]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 27513Indole-5-carbonitrileHCID 81503Bromomethylcyclopropane

Product 1

HCID 68524610HCID 68524610, compoundYield 87.4%

Conditions

Temperature
0 °C

Procedure

To a solution of 5-cyano-indole (0.15 mg, 1.05 mmol) in dry DMF (3.5 mL) sodium hydride (55% in oil) (69 mg, 1.58 mmol) was added in one portion at 0° C. The mixture was stirred at 0° C. for 30 min and (bromomethyl)-cyclopropane (0.133 mL, 1.37 mmol) was added. The resulting mixture was allowed to warm to room temperature, and stirred for 30 min. After completion monitored by TLC, reaction mixture was quenched with ice and extracted with EtOAc. The organic layer was washed with water, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (EtOAc:hexane, 1:9) to give the product as a colorless solid (180 mg, 87%). 1H NMR (CDCl3, 400 MHz,): 0.40 (m, 1H), 0.68 (m, 1H), 0.89 (m, 1H), 4.02 (d, J=6.7 Hz, 2H), 6.60 (d, J=3.2 Hz, 7.98 (s, 1H), 7.36 (d, J=3.2 Hz, 2H), 1H), 7.42 (d, J=3.4 Hz, 2H). 13C NMR (CDCl3, 100 MHz,): 4.14, 11.1, 50.9, 102.2, 110.2, 120.9, 124.3, 126.5, 128.2, 129.8, 137.6.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 30 min
  3. customAfter completion monitored by TLC, reaction mixture
  4. customwas quenched with ice
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography (EtOAc:hexane, 1:9)

Sources & evidence

ORD record
ord-7e740b1c571d439c92d8a47c4ce2e161
Source dataset
uspto-grants-2012_06
Patent number
US08207216B2

Reaction notes

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