HCID 11626285, compound → HCID 11515774, compound

HRID 1441933Notes

Reaction equation

HRID 1441933 reaction equation
C([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19](=[O:28])[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[CH:22]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[NH:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19](=[O:28])[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[CH:22]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 11626285HCID 11626285, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11515774HCID 11515774, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A nitrogen flushed mixture of 3-bromo-phenyl -carbamic acid 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester (0.218 g., ½ mmol) and 5% Pd—C (0.02 g.) in absolute ethanol (25 ml) was shaken in a par apparatus at room temperature (38° C.) under 50 psi pressure of hydrogen for 4 hours. Pd—C was then discarded through filtration. The reaction mixture was concentrated under reduced pressure and the residue was washed with dichloromethane (2×3 ml) to give 2c; yield: 0.16 g. (92.4%), m.p.: 198° C., C16H15BrN2O2, 1H NMR δ ppm (CDCl3+DMSO-d6): 1.73-1.81 (m, 2H), 2.55 (t, 2H), 3.06 (t, 2H), 6.67-6.98 (m, 4H), 6.90-7.20 (m, 2H), 7.36 (bs, 1H), 9.39 (bs, 1H), IR vmax (KBr) (cm−1): 509, 694, 758, 815, 886, 1012, 1084, 1149, 1216, 1319, 1352, 1442, 1504, 1549, 1600, 1710, 2365, 2479, 2727, 2827, 2927, 3420, 3780.

Workup

  1. customA nitrogen flushed
  2. filtrationPd—C was then discarded through filtration
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washthe residue was washed with dichloromethane (2×3 ml)

Sources & evidence

ORD record
ord-4735b34ccccf4fbd8e22e8849dae592f
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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