3-(Methoxycarbonyl)benzeneboronic acid → Methyl 2-amino-5-({1-[3-(methoxycarbonyl)phenyl]-2-methylindolizin-3-yl}carbonyl)benzoate

HRID 535446Notes

Reaction equation

HRID 535446 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)=[O:4].O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[NH2:24][C:25]1[CH:34]=[CH:33][C:32]([C:35]([C:37]2[N:45]3[C:40]([CH:41]=[CH:42][CH:43]=[CH:44]3)=[C:39](Br)[C:38]=2[CH3:47])=[O:36])=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:24][C:25]1[CH:34]=[CH:33][C:32]([C:35]([C:37]2[N:45]3[C:40]([CH:41]=[CH:42][CH:43]=[CH:44]3)=[C:39]([C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:10]=3)[C:38]=2[CH3:47])=[O:36])=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28]

Participants

6

Reactant 3

HCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 23436936Potassium phosphate dihydrateHCID 57500395Methyl 2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoate

Product 1

HCID 66653153Methyl 2-amino-5-({1-[3-(methoxycarbonyl)phenyl]-2-methylindolizin-3-yl}carbonyl)benzoateYield 65.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

0.229 g (1.27 mmol) of [3-(methoxycarbonyl)phenyl]boronic acid, 0.492 g (2.12 mmol) of potassium phosphate dihydrate and 0.024 g (0.02 mmol) of tetrakis(triphenylphosphine)palladium are added, under an argon atmosphere at ambient temperature, to 0.410 g (1.06 mmol) of methyl 2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoate in 8 ml of a DME/H2O (5/1) mixture. The reaction medium is heated at 90° C. for 18 hours. The reaction medium is extracted with dichloromethane, washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate, filtered, and then concentrated under reduced pressure. The solid obtained is purified by silica gel column chromatography, elution being carried out with dichloromethane. 309 mg of a yellow solid are obtained.

Workup

  1. extractionThe reaction medium is extracted with dichloromethane
  2. washwashed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe solid obtained
  7. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-ca3aab6099ff4c8bba625c3ea634d623
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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