Water → HCID 18999834, compound

HRID 2260117Notes

Reaction equation

HRID 2260117 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:12]2[CH:13]=[N:14][C:15]3[CH:16]=[C:17]4[CH:24]=[N:23][NH:22][C:18]4=[CH:19][C:20]=3[N:21]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].Br[CH2:26][CH2:27][O:28][C:29](=[O:31])[CH3:30].O>CN(C=O)C>[C:29]([O:28][CH2:27][CH2:26][N:22]1[C:18]2=[CH:19][C:20]3[N:21]=[C:12]([C:6]4[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([F:3])[CH:5]=4)[CH:13]=[N:14][C:15]=3[CH:16]=[C:17]2[CH:24]=[N:23]1)(=[O:31])[CH3:30].[C:29]([O:28][CH2:27][CH2:26][N:23]1[CH:24]=[C:17]2[C:18]([CH:19]=[C:20]3[C:15](=[CH:16]2)[N:14]=[CH:13][C:12]([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([F:3])[CH:5]=2)=[N:21]3)=[N:22]1)(=[O:31])[CH3:30]

Participants

7

Reactant 4

HCID 962WaterHCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 9860908HCID 9860908, compound

Product 2

HCID 18999834HCID 18999834, compoundHCID 18999846HCID 18999846, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60%; 0.35 g) is added into a stirring solution of 2.14 g of 7-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-g]quinoxaline in 30 ml of anhydrous DMF and stirred for 15 minutes, then 1.34 g of 2-bromoethylacetate is added into the mixture slowly. The resulting mixture is stirred at room temperature for 21/2 hours then poured into water and the product is filtered off, washed with water and dried. This is purified by column chromatography using 5% →20% ethylacetate in methylene chloride as eluent to obtain 1-(2-acetoxyethyl)-7-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-g]quinoxaline (m.p. 164°-166° C.) and 2-(2-acetoxyethyl)-7-(3-fluoro-4-methoxyphenyl)-2H-pyrazolo[3,4-g]quinoxaline (m.p. 175°-178° C.).

Workup

  1. stirringThe resulting mixture is stirred at room temperature for 21/2 hours
  2. filtrationthe product is filtered off
  3. washwashed with water
  4. customdried
  5. customThis is purified by column chromatography

Sources & evidence

ORD record
ord-2c9c83bbda3c426fb7f5c756e465fb60
Source dataset
uspto-grants-1995_12
Patent number
US05476851

Reaction notes

Loading…