Sodium Sulfite → HCID 22477182, compound

HRID 549079Notes

Reaction equation

HRID 549079 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2C=O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:30])C=1.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH2:12][C:11]2=[O:30])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acid2×HCID 22477256HCID 22477256, compound

Product 1

HCID 22477182HCID 22477182, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (24.3 g, Reference Example 73) in dichloromethane (700 mL), under nitrogen and at 5° C., was treated with 3-chloroperbenzoic acid (26.7 g, 70%). After stirring at 5° C. for 16 hours a further aliquot of 3-chloroperbenzoic acid (15 g, 70%) was added and stirring was continued for a further 6 hours at 5° C. The reaction mixture was then treated with sodium sulfite solution (1 L, 10%), the organic phase was separated and the aqueous phase was extracted twice with dichloromethane (200 mL). The combined organic phase and extracts were washed with water (400 mL), dried over magnesium sulfate and then evaporated. The residue was subjected to flash column chromatography on silica eluting initially with a mixture of ethyl acetate and pentane (1:3, v/v) and then with a mixture of dichloromethane and methanol (95:5, v/v) to give the title compound (11.7 g) as an orange solid.

Workup

  1. additionwas added
  2. customthe organic phase was separated
  3. extractionthe aqueous phase was extracted twice with dichloromethane (200 mL)
  4. washThe combined organic phase and extracts were washed with water (400 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. additionThe residue was subjected to flash column chromatography on silica eluting initially with a mixture of ethyl acetate and pentane (1:3
  8. additionv/v) and then with a mixture of dichloromethane and methanol (95:5

Sources & evidence

ORD record
ord-995516c04f494ff7ab9d462ddad60e4c
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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