Sodium Carbonate → HCID 11750653, compound

HRID 1694751Notes

Reaction equation

HRID 1694751 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.C(=O)([O-])[O-].[Na+].[Na+].Br[C:24]1[CH:29]=[CH:28][C:27]([S:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)(=[O:32])=[O:31])=[CH:26][CH:25]=1>O1CCOCC1.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]>[Cl:16][C:14]1[CH:13]=[CH:12][C:5]([O:6][C@@H:7]([CH3:11])[C:8]([OH:10])=[O:9])=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)(=[O:31])=[O:32])=[CH:26][CH:25]=2)[CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2531284-[(4-Bromobenzene)sulfonyl]morpholineHCID 67277298(2S)-2-(2-borono-4-chlorophenoxy)-propanoic acid

Product 1

HCID 11750653HCID 11750653, compound

Reagents, catalysts & solvents 2

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

Procedure

A mixture of the product from example 151 step (iv) (0.126 g), sodium carbonate (0.22 g), 4-[(4-bromophenyl)sulfonyl]morpholine (0.16 g) and Pd(dppf)Cl2 (0.03 g) in dioxane (10 ml) was heated under reflux for 4 h. The mixture was evaporated and purified by RVHPLC (MeCN/aqNH4Cl). Yield 0.09 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. customThe mixture was evaporated
  4. custompurified by RVHPLC (MeCN/aqNH4Cl)

Sources & evidence

ORD record
ord-64016cd5b9d6432fadcad2baf1e5266c
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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