Methyl iodide → HCID 21952653, compound

HRID 2215891Notes

Reaction equation

HRID 2215891 reaction equation
[CH3:1][S:2][C:3]1[C:11]2[NH:10][C:9]3[CH2:12][CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C:8]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH-].[K+].I[CH3:26]>COCCOC>[CH3:26][N:10]1[C:11]2[C:3]([S:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=2[C:8]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH2:12][C:9]1=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 21952650HCID 21952650, compound

Product 1

HCID 21952653HCID 21952653, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Tert-butyl 6-methylsulfanyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (7.2 g, 22.6 mmol), potassium hydroxide (6.3 g, 113 mmol), and iodomethane (32 g, 226 mmol) were combined with dry DME (110 mL) and stirred at rt for 10 h. 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-methylsulfanyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate as an oily brown residue (7.7 g, 105%). 1H NMR (CDCl3, 300 MHz) δ 7.32 (d, 1H, J=7.7 Hz), 7.12 (d, 1H, J=6.6 Hz), 7.03 (t, 1H, J=7.0 Hz), 4.61 (s, 2H), 4.08 (s, 3H), 3.85 (br s, 2H), 2.80 (br s, 2H), 2.49 (s, 3H), 1.49 (s, 9H) ppm

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-184d08e9fdb04664a647fad8bac34768
Source dataset
uspto-grants-2006_09
Patent number
US07109339B2

Reaction notes

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