Methyl iodide → HCID 86623424, compound

HRID 2111442Notes

Reaction equation

HRID 2111442 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:14][C:13](=[O:15])[CH2:12][C@@H:11]3[N:7]([CH2:8][CH2:9][CH2:10]3)[C:6]=2[N:16]=1.[C:17](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:14]([CH3:17])[C:13](=[O:15])[CH2:12][C@@H:11]3[N:7]([CH2:8][CH2:9][CH2:10]3)[C:6]=2[N:16]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86623425HCID 86623425, compound

Product 1

HCID 86623424HCID 86623424, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.4 g (0.0017 mole) of (R)-9-chloro-2,3,3a,4-tetrahydro-1H,6H-6,8,10,10b-tetraaza-benzo[e]azulen-5-one (VI-102) in 10 mL of dimethylformamide was added 1.1 g (0.0034 mole) of cesium carbonate, followed by 0.32 mL (0.0051 mole) of iodomethane. After stirring overnight, the mixture was filtered and the filtrate concentrated under reduced pressure. Purification of the residue by silica gel chromatography, eluting with hexanes-ethyl acetate (40:60-0:100) gave 0.35 g of (R)-9-chloro-6-methyl-2,3,3a,4-tetrahydro-1H,6H-6,8,10,10b-tetraaza-benzo[e]azulen-5-one (VII-102) as a light yellow solid.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customPurification of the residue by silica gel chromatography
  4. washeluting with hexanes-ethyl acetate (40:60-0:100)

Sources & evidence

ORD record
ord-80c4fc9f09c04f15bd989f8de7c83d8f
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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