1,2-Dichloroethane → 2-[4-Bromo-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl ester

HRID 521431Notes

Reaction equation

HRID 521431 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][C:14]1[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:32][O:33][C:34]([C:36]1([NH2:45])[CH2:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:37]1)=[O:35].C(Cl)CCl>CN(C=O)C>[CH3:32][O:33][C:34]([C:36]1([NH:45][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([O:11][CH2:12][CH2:13][C:14]3[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=3)[CH:4]=2)[CH2:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:37]1)=[O:35]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 45074056methyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate hydrochlorideHCID 670766394-Bromo-3-(2-m-tolyl-ethoxy)-benzoic acid

Product 1

HCID 670764352-[4-Bromo-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl esterYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of step 2 (0.410 g, 1.22 mmol) was dissolved in DMF (5 ml), EDIA (0.790 g, 6.12 mmol), HOBT (33 mg, 0.244 mmol), and 2-amino-indane-2-carboxylic acid methyl ester hydrochloride (0.246 g, 1.47 mmol) were added, the mixture was cooled in an ice bath and EDC (352 mg, 1.84 mmol) was added. The mixture was stirred overnight. The volatiles were evaporated in vacuo, the mixture was partitioned between 2 N hydrochloric acid and EA, the organic phase was dried over magnesium sulfate and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient) to give 0.56 g of the title compound.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customThe volatiles were evaporated in vacuo
  3. customthe mixture was partitioned between 2 N hydrochloric acid and EA
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-8e687f83a5664f84b48a8a3281d8a2e8
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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