Sodium Carbonate → HCID 69052745, compound

HRID 1866182Notes

Reaction equation

HRID 1866182 reaction equation
[CH2:1]([N:8]([CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31](Br)=[CH:30][CH:29]=1)[CH2:9][C@H:10]([O:18][Si](C(C)(C)C)(C)C)[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si]([O:42][C:43]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45][CH:44]=1)(C(C)(C)C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([N:8]([CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:46]2[CH:45]=[CH:44][C:43]([OH:42])=[CH:48][CH:47]=2)=[CH:30][CH:29]=1)[CH2:9][C@@H:10]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[OH:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 111078154-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 24824074HCID 24824074, compound

Product 1

HCID 69052745HCID 69052745, compoundYield 77.5%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of (2R)-N-benzyl-N-[2-(4-bromophenyl)-ethyl]-2-[[tert-butyl(dimethyl)silyl]oxy]-2-(3-chlorophenyl)ethanamine (850 mg) in 1,2-dimethoxyethane (9 ml) was added 4-[[tert-butyl(dimethyl)silyl]oxy]-phenylboronic acid (498 mg), tetrakis(triphenylphosphine)-palladium (88 mg) and aqueous solution of sodium carbonate (2M, 1.6 ml), and the mixture was stirred at 75° C. for 10 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. To a solution of the residue in tetrahydrofuran (10 ml) was added 1M tetrabutylammonium fluoride in tetrahydrofuran (3.6 ml), and the mixture was stirred at room temperature for 8 hours under nitrogen. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give 4′-[2-[N-benzyl-N-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]-1,1′-biphenyl-4-ol (540 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. additionTo a solution of the residue in tetrahydrofuran (10 ml) was added 1M tetrabutylammonium fluoride in tetrahydrofuran (3.6 ml)
  6. stirringthe mixture was stirred at room temperature for 8 hours under nitrogen
  7. customThe mixture was partitioned between ethyl acetate and water
  8. customThe organic layer was separated
  9. washwashed with water and brine
  10. dry with materialdried over magnesium sulfate
  11. customevaporated under reduced pressure
  12. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-dcaf9ce8454c4d0a916f70801451d8ce
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

Loading…