8-Iodoquinoline → (S)-5,5-dimethyl-3-(1-oxo-2-(quinolin-8-yl)-1,2,3,4-tetrahydroisoquinolin-6-yl)-4-phenyloxazolidin-2-one

HRID 525375Notes

Reaction equation

HRID 525375 reaction equation
[CH3:1][C:2]1([CH3:25])[O:6][C:5](=[O:7])[N:4]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[NH:13][CH2:12][CH2:11]3)[C@H:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.I[C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:36]=1[N:35]=[CH:34][CH:33]=[CH:32]2>>[CH3:1][C:2]1([CH3:25])[O:6][C:5](=[O:7])[N:4]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[N:13]([C:27]2[CH:28]=[CH:29][CH:30]=[C:31]4[C:36]=2[N:35]=[CH:34][CH:33]=[CH:32]4)[CH2:12][CH2:11]3)[C@H:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 177503868-IodoquinolineHCID 89813908(S)-5,5-dimethyl-3-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-4-phenyloxazolidin-2-one

Product 1

HCID 89815769(S)-5,5-dimethyl-3-(1-oxo-2-(quinolin-8-yl)-1,2,3,4-tetrahydroisoquinolin-6-yl)-4-phenyloxazolidin-2-oneYield 68.6%

Procedure

The title compound was prepared as described in General Scheme A substituting (S)-5,5-dimethyl-3-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-4-phenyloxazolidin-2-one and 8-iodoquinoline (commercially available from Synthonix, Wake Forest, N.C.). The final reaction mixture was filtered through Celite® brand filter aid with MeOH and DCM, concentrated, and purified (ISCO: 5 g cartridge, 12 g column, 0 to 40 to 80 to 100% EtOAc-heptanes) giving (S)-5,5-dimethyl-3-(1-oxo-2-(quinolin-8-yl)-1,2,3,4-tetrahydroisoquinolin-6-yl)-4-phenyloxazolidin-2-one (68.1 mg, 0.147 mmol, 68.6% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.85-8.89 (m, 1H), 8.41-8.46 (m, 1H), 7.96-8.01 (m, 1H), 7.77-7.81 (m, 1H), 7.71-7.76 (m, 1H), 7.62-7.69 (m, 2H), 7.52-7.59 (m, 1H), 7.37-7.46 (m, 3H), 7.22-7.36 (m, 3H), 5.54-5.58 (m, 1H), 3.80-4.09 (m, 2H), 3.10-3.18 (m, 2H), 1.66 (s, 3H), 0.93 (s, 3H). m/z (ESI) 464.2 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customThe final reaction mixture
  3. filtrationwas filtered through Celite® brand
  4. filtrationfilter aid with MeOH and DCM
  5. concentrationconcentrated
  6. custompurified (ISCO: 5 g cartridge, 12 g column, 0 to 40 to 80 to 100% EtOAc-heptanes)

Sources & evidence

ORD record
ord-64a6a6ddf5074befa4c475c2dc46ea81
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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