Dichloromethane → HCID 66711148, compound

HRID 1262020Notes

Reaction equation

HRID 1262020 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]2=[CH:9][CH:10]=[C:11]([CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[OH:13])[N:5]2[N:4]=1.C(Cl)Cl.ClC1C=CC=C(C(OO)=[O:31])C=1>>[CH3:1][S:2]([C:3]1[N:8]=[CH:7][C:6]2=[CH:9][CH:10]=[C:11]([CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[OH:13])[N:5]2[N:4]=1)=[O:31]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 66711729HCID 66711729, compound

Product 1

HCID 66711148HCID 66711148, compoundYield 48.2%

Procedure

(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl-methanol (0.340 g, 1.25 mmol) was dissolved in Methylene chloride (6 mL, 90 mmol) and the solution was treated with m-Chloroperbenzoic acid (0.379 g, 1.69 mmol) at room temperature. The reaction was allowed to stir until HPLC showed consumption of starting materials. The mixture was poured over saturated sodium bicarbonate and organics were extracted with dichloromethane. Combined extracts were then dried over sodium sulfate, filtered and reduced. The crude reaction mixture was then purified by Isco flash column chromatography (hexanes/ethyl acetate eluent) and combined fractions were reduced and dried under vacuum to afford 173 mg of (2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl-methanol. 1H NMR (400 MHz, CDCl3) δ 8.91 (s, 1H), 7.48 (m, 2H), 7.33 (m, 3H), 6.92 (m, 1H), 6.84 (m, 1H), 6.50 (m, 1H).

Workup

  1. customconsumption of starting materials
  2. additionThe mixture was poured over saturated sodium bicarbonate
  3. extractionorganics were extracted with dichloromethane
  4. dry with materialCombined extracts were then dried over sodium sulfate
  5. filtrationfiltered
  6. customThe crude reaction mixture
  7. customwas then purified by Isco flash column chromatography (hexanes/ethyl acetate eluent)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-41bef2515e884951b688abc582b868ae
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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