Methyl iodide → HCID 68313010, compound

HRID 1530724Notes

Reaction equation

HRID 1530724 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11]([C:16]2[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[C:18]([CH3:24])[N:17]=2)=[CH:10]3)=[CH:4][C:3]=1[OH:25].[C:26]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11]([C:16]2[N:20]([CH:21]([CH3:22])[CH3:23])[N:19]=[C:18]([CH3:24])[N:17]=2)=[CH:10]3)=[CH:4][C:3]=1[O:25][CH3:26]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136414068HCID 136414068, compound

Product 1

HCID 68313010HCID 68313010, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 13-bromo-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-12-ol (5.5 g) in acetone (30 mL) was added K2CO3 (3.03 g, 22.0 mmol) and methyl iodide (1.87 g, 13.1 mmol). The mixture was stirred at room temperature for 16 h. The mixture was concentrated and diluted with ethyl acetate (50 mL). After removal of the solvent, the residue was purified by silica gel chromatography using 1-10% MeOH in DCM as eluant to afford the desired product (3.0 g, 65% yield for two steps). LCMS m/z [M+H]+ 418.1.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with ethyl acetate (50 mL)
  3. customAfter removal of the solvent
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1ec74fe1b3794ce1be15e13345c1004b
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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