Methyl iodide → tert-butyl 5-bromo-7-(tert-butoxycarbonyl(methyl)amino)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indole-9-carboxylate

HRID 1642590Notes

Reaction equation

HRID 1642590 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:8]([O:19][CH3:20])=[C:7]2[C:3]=1[C:4]1[CH:31]=[C:30]([CH3:32])[CH:29]=[N:28][C:5]=1[N:6]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[H-].[Na+].[CH3:35]I>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]([N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH3:35])[C:8]([O:19][CH3:20])=[C:7]2[C:3]=1[C:4]1[CH:31]=[C:30]([CH3:32])[CH:29]=[N:28][C:5]=1[N:6]2[C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58880099tert-butyl 5-bromo-7-(tert-butoxycarbonylamino)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indole-9-carboxylate

Product 1

HCID 58880119tert-butyl 5-bromo-7-(tert-butoxycarbonyl(methyl)amino)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indole-9-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Compound 249 (610 mg, 1.2 mmol) in dry DMF (3 mL) was added NaH (60 mg, 1.51 mmol) at 0° C. and the mixture was stirred for 20 min. To this ice cold reaction mixture was added MeI (0.72 ml, 1.44 mmol, 2 M solution) and stirred for another 30 min. at 0° C. Slowly the temperature was raised to room temperature and stirred for an additional hour. Reaction was quenched with water and extracted with ether, washed with brine, dried over Na2SO4 and finally purified flash chromatography to furnish Compound 250 (468 mg, 75%).

Workup

  1. stirringstirred for another 30 min. at 0° C
  2. stirringstirred for an additional hour
  3. customReaction
  4. customwas quenched with water
  5. extractionextracted with ether
  6. washwashed with brine
  7. dry with materialdried over Na2SO4 and finally purified flash chromatography

Sources & evidence

ORD record
ord-8dca9b04de584decb53142546b8b7050
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

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