Dichloromethane → HCID 22477607, compound

HRID 549021Notes

Reaction equation

HRID 549021 reaction equation
CS[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:17][C:12]3=[N:13][CH:14]=[CH:15][N:16]=[C:11]3[CH:10]=2)=[CH:5][CH:4]=1.O[O:19][S:20]([O-:22])=O.[K+].Cl[CH2:25]Cl>>[CH3:25][S:20]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:17][C:12]3=[N:13][CH:14]=[CH:15][N:16]=[C:11]3[CH:10]=2)=[CH:5][CH:4]=1)(=[O:22])=[O:19]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 9813537HCID 9813537, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22477607HCID 22477607, compound

Procedure

A stirred suspension of 6-(4-methylthiophenyl)-5H-pyrrolo[2,3-b]pyrazine [0.125 g, Example 1(ah)] in dichloromethane (15 mL) was treated with TBA oxone (1.35 g). After 4 hours the reaction mixture was evaporated. The residue was subjected to flash chromatography eluting with a mixture of methanol and dichloromethane (1:1, v/v) to give the title compound as a white solid. MS: 274 (MH+). 1H NMR [(CD3)2SO]: δ 12.78 (1H, s); 8.44 (1H, s); 8.28 (3H, m); 8.04 (2H, d, J=8.8 Hz); 7.40 (1H, s); 3.27 (3H, s).

Workup

  1. customAfter 4 hours the reaction mixture was evaporated
  2. washeluting with a mixture of methanol and dichloromethane (1:1

Sources & evidence

ORD record
ord-ffda97b52c25497898fac2664fca0465
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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