Cesium carbonate → HCID 178487796, compound

HRID 633843Notes

Reaction equation

HRID 633843 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:11][C:12](=[O:38])[NH:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([CH:20]([OH:37])[CH:21]([OH:36])[CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=3)[N:26]=[CH:25][C:24]=2Cl)[CH2:16][CH2:15]1)([CH3:10])([CH3:9])[CH3:8].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:7]([O:11][C:12](=[O:38])[NH:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([CH:20]([OH:37])[CH:21]2[O:36][C:24]3[CH:25]=[N:26][C:27]4[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][C:32]=4[C:23]=3[CH2:22]2)[CH2:16][CH2:15]1)([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 178487874HCID 178487874, compound

Product 1

HCID 178487796HCID 178487796, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Cesium carbonate (3.1 g, 9.46 mmol, 2.0 eq) is added at room temperature to a stirred solution of {trans-4-[3-(3-chloro-6-methoxy-quinolin-4-yl)-1,2-dihydroxy-propyl]-cyclohexyl}-carbamic acid tert-butyl ester (2.2 g, 4.73 mmol, 1.0 eq) in dioxane (70 mL), followed by palladium(II) acetate (159 mg, 0.71 mmol, 0.15 eq) and racemic-2-di-tert-butylphosphino-1,1′-binaphthyl (283 mg, 0.71 mmol, 0.15 eq). After 3 hours stirring at 100° C., solvent is removed and the residue is extracted with dichloromethane (3×100 mL) and water (100 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated to afford {trans-4-[hydroxy-(8-methoxy-1,2-dihydro-furo[2,3-c]quinolin-2-yl)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester as a light grey solid (1.35 g, 67% yield).

Workup

  1. customsolvent is removed
  2. extractionthe residue is extracted with dichloromethane (3×100 mL) and water (100 mL)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6f53f808efdc4fd29850c16ab40ce674
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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