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

HRID 2361363Notes

Reaction equation

HRID 2361363 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)=[CH:13][N:12]=[C:11]([C:33](=[O:35])[NH2:34])[C:7]=3[NH:8]2)=[CH:4][CH:3]=1.I[Si](C)(C)C.C(OCC)(=O)C.CCCCCC>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:33]([NH2:34])=[O:35])=[N:12][CH:13]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 21226206Ethyl acetate hexaneHCID 67994872Benzyl 3-(7-bromo-1-carbamoyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate

Product 1

HCID 679947214-(3-amino-2-methylphenyl)-7-bromo-9H-pyrido[3,4-b]indole-1-carboxamideYield 52.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of benzyl 3-(7-bromo-1-carbamoyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate (0.65 g, crude from the previous step) in acetonitrile (80 mL) at 0° C. was added iodotrimethylsilane (0.67 mL, 4.91 mmol) dropwise. The mixture was stirred at room temperature for 1.5 hr, and then concentrated under vacuum. To the residue was added diethylamine (2 mL) and ethyl acetate (150 ml). The mixture was washed with water (2×40 mL) and brine (40 mL), and dried over anhydrous MgSO4. The desired product (0.243 g, 52.6% yield over two steps) was isolated as a beige solid by ISCO (40 g silica gel, solid loading, 40-70% ethyl acetate/hexane).

Workup

  1. concentrationconcentrated under vacuum
  2. additionTo the residue was added diethylamine (2 mL) and ethyl acetate (150 ml)
  3. washThe mixture was washed with water (2×40 mL) and brine (40 mL)
  4. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-47dfa53861d44a33b7cac2bb2e50fc92
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

Loading…