Trimethylsilyl iodide → 4-(3-amino-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361406Notes

Reaction equation

HRID 2361406 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3[C:14]([C:15]4[C:16]([CH3:32])=[C:17]([NH:21]C(=O)OCC5C=CC=CC=5)[CH:18]=[CH:19][CH:20]=4)=[C:13]([CH3:33])[N:12]=[C:11]([C:34](=[O:36])[NH2:35])[C:7]=3[NH:8]2)=[CH:4][CH:3]=1.I[Si](C)(C)C>C(#N)C>[NH2:21][C:17]1[C:16]([CH3:32])=[C:15]([C:14]2[C:6]3[C:5]4[C:9](=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=4)[NH:8][C:7]=3[C:11]([C:34]([NH2:35])=[O:36])=[N:12][C:13]=2[CH3:33])[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 70651685benzyl (3-(7-bromo-1-carbamoyl-3-methyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenyl)carbamate

Product 1

HCID 679952474-(3-amino-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxamideYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of benzyl (3-(7-bromo-1-carbamoyl-3-methyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenyl)carbamate (1.10 g, 2.02 mmol) in acetonitrile (100 mL) at 0° C. was added iodotrimethylsilane (1.10 mL, 8.10 mmol) dropwise. The mixture was stirred at room temperature for 1.5 h. After concentration, diethylamine (2 mL) and ethyl acetate (150 mL) were added to the residue. The mixture was washed with water (2×40 mL), washed with brine (40 mL), and dried over anhydrous sodium sulfate. Concentration under reduced pressure followed by purification by flash silica gel chromatography using a mixture of ethyl acetate in hexane (20%-35%-50%) afforded 4-(3-amino-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxamide (0.411 g, 1.00 mmol, 50% yield) as a tan solid. LC/MS M+1=409.1 and 411.1.

Workup

  1. concentrationAfter concentration, diethylamine (2 mL) and ethyl acetate (150 mL)
  2. additionwere added to the residue
  3. washThe mixture was washed with water (2×40 mL)
  4. washwashed with brine (40 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationConcentration under reduced pressure
  7. customfollowed by purification by flash silica gel chromatography
  8. additiona mixture of ethyl acetate in hexane (20%-35%-50%)

Sources & evidence

ORD record
ord-92d8aa786db04b7a9e7f2cc69ba61c67
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

Loading…