Cesium carbonate → HCID 67315446, compound

HRID 533252Notes

Reaction equation

HRID 533252 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:3]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].[C:25]1([O:35][CH2:36][CH2:37][OH:38])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]([O:38][CH2:37][CH2:36][O:35][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)=[C:3]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 69734Ethanol, 2-(1-naphthalenyloxy)-HCID 21476954HCID 21476954, compound

Product 1

HCID 67315446HCID 67315446, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

To a solution of EXAMPLE 101B (388 mg) and 2-(naphthalen-1-yloxy)ethanol (188 mg) in toluene (3 ml) was added 1,1c-binaphthyl-2-yldi-tert-butylphosphine (7.5 mg), palladium(II) acetate (5 mg) and Cs2CO3 (488 mg). The mixture was purged with argon and stirred at room temperature and then heated at 80° C. overnight. After this time the mixture was diluted with ethyl acetate (200 mL) and washed with water, brine and dried over Na2SO4. After concentration of the solvent, the residue was loaded on a silica gel column and eluted with 5% ethyl acetate in hexane to give EXAMPLE 101C.

Workup

  1. customThe mixture was purged with argon
  2. temperatureheated at 80° C. overnight
  3. additionAfter this time the mixture was diluted with ethyl acetate (200 mL)
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4
  6. washeluted with 5% ethyl acetate in hexane
  7. customto give EXAMPLE 101C

Sources & evidence

ORD record
ord-676c19b59c0c45e69357dd97370dbfae
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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