Water → 4-(8-benzyloxy-7-methoxy-3-methyl-3H-pyrazolo[3,4-c]quinolin-1-yl)benzonitrile

HRID 2404232Notes

Reaction equation

HRID 2404232 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[NH:21][N:22]=[C:23]([C:24]4[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=4)[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]([O-])([O-])=O.[K+].[K+].IC.O>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[N:21]([CH3:32])[N:22]=[C:23]([C:24]4[CH:25]=[CH:26][C:27]([C:28]#[N:29])=[CH:30][CH:31]=4)[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 666325304-(8-benzyloxy-7-methoxy-3H-pyrazolo[3,4-c]quinolin-1-yl)benzonitrile

Product 1

HCID 666321634-(8-benzyloxy-7-methoxy-3-methyl-3H-pyrazolo[3,4-c]quinolin-1-yl)benzonitrileYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(8-Benzyloxy-7-methoxy-3H-pyrazolo[3,4-c]quinolin-1-yl)benzonitrile (2.50 g, 6.15 mmol) is dissolved in N,N-dimethylformamide (72 ml). K2CO3 (1.70 g, 12.3 mmol) and iodomethane (421 μl, 6.76 mmol) are subsequently added at room temperature, and the reaction mixture is stirred for 18 h (TLC (HPTLC) monitoring). The mixture is then added to water (500 ml) and stirred for 30 min. The precipitate obtained is filtered off with suction and chromatographed over flash silica gel (120 g, solvent gradient cyclohexane/0-100% by vol. of ethyl acetate/0-40% by vol. of ethanol). The residue from the product fractions is suspended in 2-propanol, filtered off with suction and dried in a high vacuum, giving 4-(8-benzyloxy-7-methoxy-3-methyl-3H-pyrazolo[3,4-c]quinolin-1-yl)benzonitrile (1.79 g, 4.27 mmol) as a solid having a melting point of 230.4° C. MS: 421.1 (M+H+), TLC (HPTLC): Rf=0.44 (ethyl acetate/ethanol 8:1, parts by volume).

Workup

  1. stirringstirred for 30 min
  2. customThe precipitate obtained
  3. filtrationis filtered off with suction
  4. customchromatographed over flash silica gel (120 g, solvent gradient cyclohexane/0-100% by vol. of ethyl acetate/0-40% by vol. of ethanol)
  5. filtrationfiltered off with suction
  6. customdried in a high vacuum

Sources & evidence

ORD record
ord-dbfb7d0a83ae4e3c957d847a6ba07083
Source dataset
uspto-grants-2014_08
Patent number
US08802712B2

Reaction notes

Loading…