Methyl iodide → HCID 68819707, compound

HRID 735211Notes

Reaction equation

HRID 735211 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[NH:16][C:15]4[CH2:18][CH2:19][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][C:14]=4[C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[K+].I[CH3:32]>COCCOC>[CH3:32][N:16]1[C:17]2[C:9]([S:8][C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)=[CH:10][CH:11]=[CH:12][C:13]=2[C:14]2[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19][CH2:18][C:15]1=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 68816919HCID 68816919, compound

Product 1

HCID 68819707HCID 68819707, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Tert-butyl 6-[(4-methylphenyl)sulfanyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (22.6 mmol), potassium hydroxide (113 mmol), and iodomethane (226 mmol) were combined with dry DME (110 mL) and stirred at room temperature for 10 hours. The reaction was then filtered and the residue washed with chloroform. The filtrate was concentrated under reduced pressure to give tert-butyl 5-methyl-6-[(4-methylphenyl)sulfanyl]-1,3,4,5,-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (95%).

Workup

  1. filtrationThe reaction was then filtered
  2. washthe residue washed with chloroform
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-645e1327b54a4c119af4aeb72fb2e3da
Source dataset
uspto-grants-2009_09
Patent number
US07592454B2

Reaction notes

Loading…