Trimethylsilyl iodide → 5'-Chloro-4-methyl-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-4-ylamine

HRID 855841Notes

Reaction equation

HRID 855841 reaction equation
C(OC(=O)[NH:10][C:11]1([CH3:24])[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1.I[Si](C)(C)C>C(#N)C>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([N:14]2[CH2:15][CH2:16][C:11]([NH2:10])([CH3:24])[CH2:12][CH2:13]2)=[N:18][CH:19]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 66756881(5'-chloro-4-methyl-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-4-yl)-carbamic acid benzyl ester

Product 1

HCID 178608295'-Chloro-4-methyl-3,4,5,6-tetrahydro-2H-(1,2')bipyridinyl-4-ylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of (5′-chloro-4-methyl-3,4,5,6-tetrahydro-2H-(1,2′)bipyridinyl-4-yl)-carbamic acid benzyl ester (0.060 g, 0.17 mmol) in acetonitrile (1.0 mL) at room temperature was added iodotrimethysilane (0.04 mL, 0.25 mmol). The reaction mixture was stirred at 50° C. for 30 minutes, concentrated under reduced pressure, and purified by flash chromatography with 3% methanol in dichloromethane to provide titled compound. MS (CI) m/z 226 (M+1)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by flash chromatography with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-2843488d4c304301895b9b28b542ab26
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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