Sodium Sulfite → 3,8-Difluoro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

HRID 15137

Reaction equation

HRID 15137 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]=[C:7]([F:16])[C:8](=[O:15])[N:9]3CC(=C)C=1[C:10]=23.S([O-])([O-])=O.[Na+].[Na+].[C:23]([OH:27])([CH3:26])([CH3:25])[CH3:24].[OH2:28]>>[F:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]=[C:7]([F:16])[C:8](=[O:15])[N:9]3[CH2:25][C:23]([OH:27])([CH2:26][OH:28])[C:24]=1[C:10]=23

Participants

4

Reactant 3

HCID 24437Sodium SulfiteHCID 675274023,8-Difluoro-4-methylidene-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-oneHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 236342743,8-Difluoro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-oneYield 97%

Procedure

A solution of 3,8-difluoro-4-methylidene-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (631 mg, 2.9 mmol) in tert-butanol/water (30 ml/30 ml) was treated with AD mix alpha (4.3 g) under argon. After 18 hours stirring the reaction mixture was treated with saturated sodium sulphite solution (30 ml). After 10 minutes stirring the mixture was extracted with 20% methanol in dichloromethane (3×300 ml). The organic extracts were dried over magnesium sulphate and evaporated affording a white solid (710 mg, 97%).

Workup

  1. additionmix alpha (4.3 g) under argon
  2. stirringAfter 10 minutes stirring the mixture
  3. extractionwas extracted with 20% methanol in dichloromethane (3×300 ml)
  4. dry with materialThe organic extracts were dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-c9aded2d0f824bf9b94d7c7d4dcc8f67
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Linked notes

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