Methanol → 5-Bromo-7-(4-methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

HRID 1261890Notes

Reaction equation

HRID 1261890 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)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CO.O1CCCC1.[Br:29]N1C(=O)CCC1=O>>[Br:29][C:13]1[CH:12]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=2)[N:19]2[C:14]=1[CH:15]=[N:16][C:17]([S:20][CH3:21])=[N:18]2

Participants

5

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 667120257-(4-Methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 667117075-Bromo-7-(4-methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazineYield 55%

Procedure

Into a 30 mL vial, 7-(4-Methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.205 g, 0.000642 mol), Methanol (4 mL, 0.1 mol) and Tetrahydrofuran (9 mL, 0.1 mol) were added. N-Bromosuccinimide (0.137 g, 0.000770 mol) was added portion wise over 5 minutes. The reaction was stirred at room temperature over night. The solvent was removed under vacuum. The solid was partitioned with water and filtered to give a yellow solid. The solid was washed with cold methanol to give 5-Bromo-7-(4-methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid (140 mg, 55%). NMR 1H (DSMO-d6)-9.01 (s, 1H), 8.48 (d, 2H, J=8.48 Hz), 8.07 (d, 2H, J=8.53 Hz), 7.79 (s, 1H), 3.28 (s, 3H), 2.62 (s, 3H)

Workup

  1. customThe solvent was removed under vacuum
  2. customThe solid was partitioned with water
  3. filtrationfiltered
  4. customto give a yellow solid
  5. washThe solid was washed with cold methanol

Sources & evidence

ORD record
ord-33d93691d1a8434796b4ff3d4ad59404
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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