Citric Acid → HCID 66990697, compound

HRID 454771Notes

Reaction equation

HRID 454771 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].B1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:17]=2)OC(C)(C)C(C)(C)O1.Br[C:31]1[CH:43]=[CH:42][C:34]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[C:33]([NH:44][C:45]([C:47]2[CH:48]=[N:49][CH:50]=[C:51]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH:52]=2)=[O:46])[CH:32]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.COCCOC.O>[C:26]([O:25][C:23]([O:22][C:18]1[CH:17]=[C:16]([C:31]2[CH:43]=[CH:42][C:34]([C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])=[C:33]([NH:44][C:45]([C:47]3[CH:48]=[N:49][CH:50]=[C:51]([C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[CH:52]=3)=[O:46])[CH:32]=2)[CH:21]=[CH:20][CH:19]=1)=[O:24])([CH3:27])([CH3:28])[CH3:29]

Participants

9

Reactant 4

HCID 311Citric AcidHCID 10340Sodium CarbonateHCID 27739553-(tert-Butoxycarbonyloxy)phenylboronic acid pinacol esterHCID 58508430Tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoate

Product 1

HCID 66990697HCID 66990697, compound

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Water (0.6 mL), sodium carbonate (58 mg), tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbonate (85 mg), and bis(triphenylphosphine)palladium(II) dichloride (3.0 mg) were added to an ethylene glycol dimethyl ether (2.0 mL) suspension of tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoate (0.10 g), followed by heating to reflux under a nitrogen atmosphere for 1 hour. The reaction mixture was cooled to room temperature, and then ethyl acetate and a 10% aqueous solution of citric acid were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-80% hexane/ethyl acetate] to obtain tert-butyl 4-(3-(tert-butoxycarbonyl)oxyphenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate.

Workup

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 1 hour
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 95-80% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-f1d1e6e4d93643968635cd94ef417b05
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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