Potassium Carbonate → 2-(3-Fluoro-5-hydroxy-4-methoxy-benzoylamino)-indane-2-carboxylic acid methyl ester

HRID 521461Notes

Reaction equation

HRID 521461 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([F:16])[C:13]=1[O:14][CH3:15])[C:8]([OH:10])=O)(=O)C.Cl.[CH3:18][O:19][C:20]([C:22]1([NH2:31])[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1)=[O:21].C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:18][O:19][C:20]([C:22]1([NH:31][C:8](=[O:10])[C:7]2[CH:6]=[C:5]([OH:4])[C:13]([O:14][CH3:15])=[C:12]([F:16])[CH:11]=2)[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1)=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 45074056methyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate hydrochlorideHCID 670767283-Acetoxy-5-fluoro-4-methoxy-benzoic acid

Product 1

HCID 670766132-(3-Fluoro-5-hydroxy-4-methoxy-benzoylamino)-indane-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound of step 3 (120 mg, 0.526 mmol) was reacted with 2-amino-indane-2-carboxylic acid methyl ester hydrochloride in analogy to step 1 of example 15. The obtained product was dissolved in methanol (0.77 ml), potassium carbonate (2 mg) was added, and the mixture was stirred at room temperature for 30 min. The solvent was evaporated, the residue was partitioned between EA and a saturated sodium chloride solution, and the aqueous phase extracted with EA. The combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness to give 60 mg of the title compound.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between EA
  3. extractiona saturated sodium chloride solution, and the aqueous phase extracted with EA
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-59fb5bba0a5e41b397050627ecbb17ba
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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