Citric Acid → HCID 178526453, compound

HRID 271706Notes

Reaction equation

HRID 271706 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](OB(O)O)=[CH:4][CH:3]=1.Br[C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[C:16]([OH:19])=[N:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC(C)=O.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]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]2[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[C:16]([OH:19])=[N:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 10340Sodium CarbonateHCID 17810664p-Chlorophenylboric acidHCID 178418997HCID 178418997, compound

Product 1

HCID 178526453HCID 178526453, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 180AcetoneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

23.5 g (150 mmol) 4-chlorophenyl-boric acid are added under argon to a solution of 22.1 g (101 mmol) 5-bromo-3-nitro-pyridin-2-ol, 200 mL (400 mmol) of a 2 M Na2CO3 solution and 731 mg (1.00 mmol) Pd(dppf)Cl2 in 400 mL acetone and 80 mL water. The reaction mixture is stirred for 18 h at 60° C. Acetone is eliminated i.vac. and the residue is adjusted to pH 7 with 160 mL 1 M citric acid. The aqueous phase is extracted three times with EtOAc and once with MeOH. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The residue is triturated with EtOAc.

Workup

  1. extractionThe aqueous phase is extracted three times with EtOAc
  2. dry with materialThe organic phase is dried over MgSO4
  3. customThe residue is triturated with EtOAc

Sources & evidence

ORD record
ord-62387ac163374b468465cac05fefecb2
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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