Methanol → HCID 66711390, compound

HRID 1261898Notes

Reaction equation

HRID 1261898 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][CH:13]=3)[N:5]2[N:4]=1.O1CCCC1.CO.[Br:25]N1C(=O)CCC1=O>>[Br:25][C:9]1[CH:10]=[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:5]2[C:6]=1[CH:7]=[N:8][C:3]([S:2][CH3:1])=[N:4]2

Participants

5

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 574161182-(Methylsulfanyl)-7-phenylpyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66711390HCID 66711390, compoundYield 87%

Procedure

Into a 30 mL vial, 2-Methylsulfanyl-7-phenyl-pyrrolo[2,1-f][1,2,4]triazine (0.295 g, 0.00122 mol), Tetrahydrofuran (10 mL, 0.1 mol) and Methanol (5 mL, 0.1 mol) were added. N-Bromosuccinimide (0.239 g, 0.00134 mol) was added over 10 minutes. The reaction was stirred at room temperature overnight. The solvent was removed under vacuum. The solid was partitioned with water, filtered and washed with water to give a yellow solid. The solid was dried under vacuum over night to give 5-Bromo-2-methylsulfanyl-7-phenyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid (0.34 g, 87%). NMR 1H (DSMO-d6)-8.93 (s, 1H), 8.19 (d, 2H, J=7.61 Hz), 7.61 (s, 1H), 7.53 (t, 2H, J=8.60 Hz), 7.42 (t, 1H, J=7.37), 2.58 (s, 3H)

Workup

  1. customThe solvent was removed under vacuum
  2. customThe solid was partitioned with water
  3. filtrationfiltered
  4. washwashed with water
  5. customto give a yellow solid
  6. customThe solid was dried under vacuum over night

Sources & evidence

ORD record
ord-d4a06b3e10f742b4b41c005e4226a3b1
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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