Water → HCID 66560940, compound

HRID 1910049Notes

Reaction equation

HRID 1910049 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=O)[CH2:14][OH:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:17](#[N:21])[CH2:18][C:19]#[N:20].C(NCC)C.O>CN(C=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[C:18]([C:19]#[N:20])=[C:17]([NH2:21])[O:15][CH:14]=3)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8010MalononitrileHCID 8021DiethylamineHCID 66560939HCID 66560939, compound

Product 1

HCID 66560940HCID 66560940, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-hydroxyethanone (0.53 g, 2.41 mmol) and malononitrile (176 mg, 2.66 mmol, 1.1 equiv) in DMF (4 mL) chilled in an ice bath was added diethylamine (380 uL, 3.63 mmol, 1.5 equiv) over a 3 minute period. The resulting mixture was stirred in the ice bath for another 20 minutes, and then the ice bath was removed. The brownish suspension was stirred at ambient temp for 2 hours. LCMS showed product formed in 75%. To the suspension was added 20 mL of water. The warm suspension was filtered. The cake was washed with water, and dried under house vacuum overnight to give 4-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-amino-3-furancarbonitrile (360 mg) as beige solids. LC-MS (ES) m/z=268 [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. customthe ice bath was removed
  3. customformed in 75%
  4. filtrationThe warm suspension was filtered
  5. washThe cake was washed with water
  6. customdried under house vacuum overnight

Sources & evidence

ORD record
ord-75f91148576c419f81fd919f0c382329
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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