Sodium Carbonate → HCID 69102258, compound

HRID 2220427Notes

Reaction equation

HRID 2220427 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH2:19][C@H:20]([OH:27])[C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[CH2:28]([O:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][C:38]=1[C:39]([O:41][CH3:42])=[O:40])[CH:29]([CH3:31])[CH3:30].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:14]([O:13][C:12]([N:11]([CH2:19][C@H:20]([OH:27])[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:35]2[CH:36]=[CH:37][C:38]([C:39]([O:41][CH3:42])=[O:40])=[C:33]([O:32][CH2:28][CH:29]([CH3:31])[CH3:30])[CH:34]=2)=[CH:3][CH:4]=1)=[O:18])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 24824482HCID 24824482, compoundHCID 86598957HCID 86598957, compound

Product 1

HCID 69102258HCID 69102258, compoundYield 92.7%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of tert-butyl [3-(4-bromophenyl)propyl]-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]carbamate (312 mg), [3-isobutoxy-4-(methoxycarbonyl)phenyl]boronic acid (207 mg), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (58.4 mg) and 1,1′-bis(diphenylphosphino)ferrocene (7.93 mg) in N,N-dimethylformamide (3.12 ml) was added 2.0M aqueous sodium carbonate solution (1.25 ml) and the mixture was stirred at 90° C. for 2.5 hours. After cooling to room temperature, palladium was removed by filtration through a Celite cake. The mixture was extracted with ethyl acetate and the extract was washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave a crude product which was purified by column chromatography on silica gel (hexane/ethyl acetate=1/1) to give methyl 4′-[3-[(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]-propyl]-3-isobutoxy-4-biphenylcarboxylate (374 mg) as a yellow solid (foam).

Workup

  1. temperatureAfter cooling to room temperature
  2. custompalladium was removed by filtration through a Celite cake
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration
  7. customfollowed by evaporation under reduced pressure
  8. customgave a crude product which
  9. customwas purified by column chromatography on silica gel (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-13c2b630dba9448194dc35feeca2feb5
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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