Sodium Carbonate → HCID 11582566, compound

HRID 16100Notes

Reaction equation

HRID 16100 reaction equation
B([C:4]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:5]=1[O:6][C@@H:7]([CH3:11])[C:8]([OH:10])=[O:9])(O)O.Br[C:18]1[CH:32]=[CH:31][C:21]([C:22]([N:24]([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])=[O:23])=[C:20]([F:33])[CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>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].O1CCOCC1>[CH3:27][CH:25]([N:24]([CH:28]([CH3:30])[CH3:29])[C:22]([C:21]1[CH:31]=[CH:32][C:18]([C:4]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:5]=2[O:6][C@@H:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:19][C:20]=1[F:33])=[O:23])[CH3:26]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 672771854-bromo-2-fluoro-N,N-bis(1-methylethyl)-benzamideHCID 67277298(2S)-2-(2-borono-4-chlorophenoxy)-propanoic acid

Product 1

HCID 11582566HCID 11582566, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

The product of step c) (200 mg), the product of step d) (200 mg), Pd(dppf)Cl2 (60 mg), sodium carbonate (350 mg) and dioxan (5 ml) were charged to a flask and heated at reflux for 24 h, then cooled to room temp and filtered (hyflo). The filtrate was concentrated in vacuo, then purified by reverse phase HPLC to give the title compound. Yield 22 mg

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. filtrationfiltered (hyflo)
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-a10d245fc92c400e98ec2b3607f30896
Source dataset
uspto-grants-2010_06
Patent number
US07737135B2

Reaction notes

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