Dichloromethane → HCID 136360288, compound

HRID 1262384Notes

Reaction equation

HRID 1262384 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]2=[CH:9][CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[N:5]2[N:4]=1.C(Cl)Cl.C1C=C(Cl)C=C(C(OO)=[O:30])C=1>>[CH3:1][S:2]([C:3]1[N:8]=[CH:7][C:6]2=[CH:9][CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[N:5]2[N:4]=1)=[O:30]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 136360287HCID 136360287, compound

Product 1

HCID 136360288HCID 136360288, compoundYield 60%

Procedure

2-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenol (1.915 g, 7.442 mmol) and Methylene chloride (50 mL, 800 mmol) were combined in a flask. m-CPBA 70-75% (70:30, m-Chloroperbenzoic acid:3-Chlorobenzoic acid, 1.835 g, 7.444 mmol) was added over 10 minutes. The reaction was stirred at room temperature for 10 minutes. Reaction was concentrated and purified by normal phase silica gel chromatography eluting with ethyl acetate to obtain a brown solid, 2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenol (1.2 g, 60%). LCMS: m/z=274.01 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 9.98 (br s, 1H), 9.29 (s, 1H), 7.80 (m, 1H), 7.46 (d, 1H, J=4.7 Hz), 7.30 (m, 2H), 7.03 (d, 1H, J=8.2 Hz), 6.96 (m, 1H), 2.93 (s, 3H).

Workup

  1. customReaction
  2. concentrationwas concentrated
  3. custompurified by normal phase silica gel chromatography
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d5b3bdfadb234a3fb54a5af7c17a53b0
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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