Water → HCID 18999800, compound

HRID 2260114Notes

Reaction equation

HRID 2260114 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].[C:25](OC(=O)C)(=[O:27])[CH3:26].O>C1COCC1>[C:25]([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:27])[CH3:26].[C:25]([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[CH2:24][NH:23]1)(=[O:27])[CH3:26]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic Anhydride2×HCID 24758Sodium hydrideHCID 9860908HCID 9860908, compound

Product 2

HCID 18999800HCID 18999800, compoundHCID 69840660HCID 69840660, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-colded suspension of NaH (0.029 g) in 30 ml of anhydrous THF under N2 is added 7-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-g]quinoxaline (0.30 g). The orange-red mixture is stirred at the same temperature for 5 minutes, then acetic anhydride (0.122 g) is added dropwise to the mixture. A yellow solid forms during the acetic anhydride additions. The resulting mixture is stirred at room temperature overnight. The mixture is poured into water. The yellow solid is filtered, washed with water then with ether and dried. The product is purified by column chromatography eluting with 15% ethylacetate in hexane, 25% ethylacetate in hexane then 5% ethylacetate in methylene chloride to obtain 1-acetyl-7-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-g]quinoxaline (m.p. 261°-265° C.) and 1-acetyl-7-(3-fluoro-4-methoxyphenyl)-2H-pyrazolo[3,4-g]quinoxaline.

Workup

  1. stirringThe resulting mixture is stirred at room temperature overnight
  2. filtrationThe yellow solid is filtered
  3. washwashed with water
  4. dry with materialwith ether and dried
  5. customThe product is purified by column chromatography
  6. washeluting with 15% ethylacetate in hexane, 25% ethylacetate in hexane

Sources & evidence

ORD record
ord-b0076ce25ed6485da41c3f8995907882
Source dataset
uspto-grants-1995_12
Patent number
US05476851

Reaction notes

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