Dichloromethane → 2-Methanesulfinyl-7-(4-methanesulfonyl-phenyl)-5-methyl-pyrrolo[2,1-f][1,2,4]triazine
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:19]3[C:14]([CH:15]=[N:16][C:17]([S:20][CH3:21])=[N:18]3)=[C:13]([CH3:22])[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(Cl)Cl.C1C=C(Cl)C=C(C(OO)=[O:34])C=1>>[CH3:21][S:20]([C:17]1[N:16]=[CH:15][C:14]2=[C:13]([CH3:22])[CH:12]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=3)[N:19]2[N:18]=1)=[O:34]Participants
Procedure
Into a 30 mL vial, [A] 7-(4-Methanesulfonyl-phenyl)-5-methyl-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.260 g, 0.000780 mol) and Methylene chloride (20 mL, 0.3 mol) were added. m-CPBA 70-75% (70:30, m-Chloroperbenzoic acid:3-Chlorobenzoic acid, 0.211 g, 0.000858 mol) was added and stirred at room temperature overnight. The reaction was partitioned with DCM and saturated NaHCO3. The organic was separated and washed with water then Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The organic was removed under vacuum to give a solid. The solid was triturated with Et2O and filtered to give 2-Methanesulfinyl-7-(4-methanesulfonyl-phenyl)-5-methyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid (0.20 g, 73%) NMR 1H (CDCl3-d)-8.99 (s, 1H), 8.24 (d, 2H, J=8.45 Hz), 8.08 (d, 2H, J=8.40 Hz), 7.28 (s, 1H), 3.10 (s, 3H), 3.02 (bs, 4H), 2.54 (s, 3H)
Workup
- customThe reaction was partitioned with DCM and saturated NaHCO3
- customThe organic was separated
- washwashed with water
- dry with materialBrine and dried over Na2SO4
- filtrationThe solid was filtered
- washwashed with DCM
- customThe organic was removed under vacuum
- customto give a solid
- customThe solid was triturated with Et2O
- filtrationfiltered
Sources & evidence
- ORD record
- ord-ba8ea027412448a7a6018e6d522246f7
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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