Cesium carbonate → Tert-butyl (1-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

HRID 339671Notes

Reaction equation

HRID 339671 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13]1)[CH:8]=[CH:7]2.[NH:19]1[CH2:24][CH2:23][CH:22]([CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:21][CH2:20]1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:29]([O:28][C:27](=[O:33])[NH:26][CH2:25][CH:22]1[CH2:21][CH2:20][N:19]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[C:9]([CH:12]2[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13]2)[CH:8]=[CH:7]3)[CH2:24][CH2:23]1)([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 672343698-Bromo-2-(2,2-dimethyl-1,3-dioxolan-4-yl)quinoline

Product 1

HCID 86654343Tert-butyl (1-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

To 8-bromo-2-(2,2-dimethyl-1,3-dioxolan-4-yl)quinoline (101 mg, 0.328 mmol) in toluene (1.3 mL) was added tert-butyl piperidin-4-ylmethylcarbamate (84.3 mg, 0.393 mmol), Pd(OAc)2 (7.3 mg, 0.033 mmol), Binap-rac (25 mg, 0.039 mmol) and Cs2CO3 (235 mg, 0.721 mmol). The reaction was purged twice with nitrogen and heated at reflux overnight. The reaction mixture was cooled to ambient temperature and filtered through Celite, and the solids were washed with EtOAc (20 mL). The filtrate was concentrated, and the crude material was purified by silica gel chromatography (EtOAc/Hexane 1:6) provided final product.

Workup

  1. customThe reaction was purged twice with nitrogen
  2. temperatureheated
  3. temperatureat reflux overnight
  4. filtrationfiltered through Celite
  5. washthe solids were washed with EtOAc (20 mL)
  6. concentrationThe filtrate was concentrated
  7. customthe crude material was purified by silica gel chromatography (EtOAc/Hexane 1:6)

Sources & evidence

ORD record
ord-e7f4afae2bc24b91ab44d0ceb62899ec
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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