Hydrochloric Acid → HCID 66653176, compound

HRID 535459Notes

Reaction equation

HRID 535459 reaction equation
Br[CH2:2][CH2:3][O:4][CH3:5].C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:12][C:13]1[CH:22]=[CH:21][C:20]([C:23]([C:25]2[N:33]3[C:28]([CH:29]=[CH:30][CH:31]=[CH:32]3)=[C:27]([OH:34])[C:26]=2[CH3:35])=[O:24])=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16].Cl>CN(C=O)C.O>[NH2:12][C:13]1[CH:22]=[CH:21][C:20]([C:23]([C:25]2[N:33]3[C:28]([CH:29]=[CH:30][CH:31]=[CH:32]3)=[C:27]([O:34][CH2:2][CH2:3][O:4][CH3:5])[C:26]=2[CH3:35])=[O:24])=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 57500359HCID 57500359, compound

Product 1

HCID 66653176HCID 66653176, compoundYield 40.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.161 g (1.16 mmol) of 1-bromo-2-methoxyethane and 0.359 mg (1.16 mmol) of caesium carbonate are added, under an inert atmosphere at ambient temperature, to 0.313 g (0.97 mmol) of methyl 2-amino-5-{[1-hydroxy-2-methylindolizin-3-yl]-carbonyl}benzoate in 10 ml of DMF. The reaction medium is stirred for 24 hours at ambient temperature, hydrolysed with water, and then acidified with a 1N aqueous solution of hydrochloric acid. The aqueous phase is extracted with ethyl acetate. The organic phase obtained is 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 a dichloromethane/methanol (95/5) mixture. 150 mg of a yellow oil are obtained.

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. customThe organic phase obtained
  3. washis washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe solid obtained
  8. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-983cc89b20914e898d02c001f191af46
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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