Dichloromethane → 7-[3-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-2-(methylsulfinyl)pyrrolo[2,1-f][1,2,4]triazine

HRID 1262411Notes

Reaction equation

HRID 1262411 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[O:12]=[S:13]1(=[O:35])[CH2:17][CH2:16][CH2:15][N:14]1[C:18]1[CH:19]=[C:20]([C:24]2[N:32]3[C:27]([CH:28]=[N:29][C:30]([S:33][CH3:34])=[N:31]3)=[CH:26][CH:25]=2)[CH:21]=[CH:22][CH:23]=1.C(Cl)Cl>>[O:35]=[S:13]1(=[O:12])[CH2:17][CH2:16][CH2:15][N:14]1[C:18]1[CH:19]=[C:20]([C:24]2[N:32]3[C:27]([CH:28]=[N:29][C:30]([S:33]([CH3:34])=[O:9])=[N:31]3)=[CH:26][CH:25]=2)[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 667117407-[3-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 667121237-[3-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-2-(methylsulfinyl)pyrrolo[2,1-f][1,2,4]triazineYield 90.1%

Procedure

m-Chloroperbenzoic acid (0.380 g, 1.54 mmol) was added to a solution of 7-[3-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine (0.515 g, 1.43 mmol) in Methylene chloride (30.0 mL, 468 mmol). The reaction was quenched at 30 min by the addition of satd. NaHCO3 (50 mL). The mixture was stirred vigorously, sept. and ext. with DCM (3×15 mL). The comb. org. was washed with 1:1 brine:satd. NaHCO3 (50 mL) and dried over sodium sulfate. After conc. in vacuo, the residue was purified on the ISCO (load onto 3.4 g silica, 40 g column, 20-100% EtOAc:Hex, then to 10% MeOH:EtOAc, then 10% MeOH:DCM) to afford 7-[3-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-2-(methylsulfinyl)pyrrolo[2,1-f][1,2,4]triazine (0.485 g, 90%). 1H-NMR (DMSO-d6): 9.34 (s, 1H), 8.16 (s, 1H), 7.95 (d, 1H, J=7.9 Hz), 7.72 (d, 1H, J=4.9 Hz), 7.55 (m, 1H), 7.34 (m, 2H), 3.87 (t, 2H, J=6.5 Hz), 3.57 (t, 2H, J=7.4 Hz), 2.99 (s, 3H), 2.44 (m, 2H).

Workup

  1. customThe reaction was quenched at 30 min by the addition of satd
  2. washwas washed with 1:1 brine
  3. dry with materialNaHCO3 (50 mL) and dried over sodium sulfate
  4. customAfter conc. in vacuo, the residue was purified on the ISCO (load onto 3.4 g silica, 40 g column, 20-100% EtOAc

Sources & evidence

ORD record
ord-5fa3e12d67e04b65b3b42a828c22da85
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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