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Potassium Phosphate, Tribasic → 3-[5-(5-Chloropyridin-2-yl)-2-ethylphenyl]bicyclo[3.2.1]octane-2,4-dione

HRID 72267
Notes
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Reaction equation

HRID 72267 reaction equation
[O:1]=[C:2]1[CH:8]([C:9]2[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][C:14]=2[CH2:15][CH3:16])[C:7](=[O:20])[CH:6]2[CH2:21][CH:3]1[CH2:4][CH2:5]2.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][N:32]=1.[Na].[Na].[Na].S(C1C=C(P(C2C=CC=C(S(O)(=O)=O)C=2)C2C=CC=C(S(O)(=O)=O)C=2)C=CC=1)(O)(=O)=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(#N)C>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C:11]2[CH:12]=[CH:13][C:14]([CH2:15][CH3:16])=[C:9]([CH:8]3[C:2](=[O:1])[CH:3]4[CH2:21][CH:6]([CH2:5][CH2:4]4)[C:7]3=[O:20])[CH:10]=2)=[N:32][CH:33]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 8170982-Bromo-5-chloropyridineHCID 684806443-(2,4-Dioxobicyclo[3.2.1]oct-3-yl)-4-ethylphenylboronic acidHCID 86657037CID 86657037

Product 1

HCID 684864883-[5-(5-Chloropyridin-2-yl)-2-ethylphenyl]bicyclo[3.2.1]octane-2,4-dione

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a microwave vial containing 3-(2,4-dioxobicyclo[3.2.1]oct-3-yl)-4-ethylphenylboronic acid (0.15 g, 0.52 mmol) and potassium phosphate (0.667 g, 3.15 mmol) is added 2-bromo-5-chloropyridine (0.121 g, 0.63 mmol), palladium acetate (4.0 mg, 0.016 mmol) and tris(3-sulfophenyl)phosphine trisodium salt (21 mg, 0.038 mmol). A degassed solvent mixture of water/acetonitrile (1.6 ml, 2:1 ratio) is then added, followed by flushing with nitrogen, then stirring at ambient temperature for 5 minutes before heating at 160° C. under microwave irradiation for 15 minutes. After cooling to room temperature the reaction is partitioned between 2M aqueous hydrochloric acid and dichloromethane, and the organic phase is separated. The aqueous phase is further extracted with dichloromethane and all organic fractions are combined then evaporated. The residue is purified by preparative reverse-phase HPLC to give 3-[5-(5-chloropyridin-2-yl)-2-ethylphenyl]bicyclo[3.2.1]octane-2,4-dione.

Workup

  1. additionis then added
  2. customby flushing with nitrogen
  3. temperaturebefore heating at 160° C. under microwave irradiation for 15 minutes
  4. temperatureAfter cooling to room temperature the reaction
  5. customis partitioned between 2M aqueous hydrochloric acid and dichloromethane
  6. customthe organic phase is separated
  7. extractionThe aqueous phase is further extracted with dichloromethane
  8. customall organic fractions are combined then evaporated
  9. customThe residue is purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-e85d6ce6ab204b93892985b05e1aa092
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08828908B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes