1,2-Dichloroethane → 3-methoxy-4-[5-(4,4,4-trifluoro-2-methyl-butylcarbamoyl)-1H-indol-3-ylmethyl]-benzoic acid methylester

HRID 1739591Notes

Reaction equation

HRID 1739591 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][C:4]=1[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([OH:17])=O)[CH:13]=2)[NH:8][CH:7]=1.ClCCCl.C(N(CC)CC)C.Cl.[F:38][C:39]([F:46])([F:45])[CH2:40][CH:41]([CH3:44])[CH2:42][NH2:43]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:25][O:24][C:22](=[O:23])[C:20]1[CH:19]=[CH:18][C:4]([CH2:5][C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:15](=[O:17])[NH:43][CH2:42][CH:41]([CH3:44])[CH2:40][C:39]([F:46])([F:45])[F:38])[CH:13]=3)[NH:8][CH:7]=2)=[C:3]([O:2][CH3:1])[CH:21]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 103372503-(2-methoxy-4-methoxycarbonyl-benzyl)-1H-indole-5-carboxylic acidHCID 21841122136564-89-1

Product 1

HCID 538245783-methoxy-4-[5-(4,4,4-trifluoro-2-methyl-butylcarbamoyl)-1H-indol-3-ylmethyl]-benzoic acid methylesterYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(2-methoxy-4-methoxycarbonyl-benzyl)-1H-indole-5-carboxylic acid (1.7 grams, 5.00 mmol) in methylene chloride (50 mL), was added 4-dimethylaminopyridine (0.67 grams, 5.50 mmol), 1,2-dichloroethane (1.06 grams, 5.50 mmol), triethylamine (0.73 mL, 5.25 mmol) and 4,4,4-trifluoro-2-methylbutylamine hydrochloride (0.93 grams, 5.25 mmol). The resulting solution was stirred 12 hours, at room temperature, then diluted with methylene chloride. The solution was washed with 1 M hydrochloric acid (aq), then the organics were dried over magnesium sulfate. Concentration in vacuo followed by trituration of the crude product in a 2:1 ratio of ether:hexanes gave 3-methoxy-4-[5-(4,4,4-trifluoro-2-methyl-butylcarbamoyl)-1H-indol-3-ylmethyl]-benzoic acid methylester (1.88 grams, 82% yield).

Workup

  1. washThe solution was washed with 1 M hydrochloric acid (aq)
  2. dry with materialthe organics were dried over magnesium sulfate
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-ad1b5704e314437b895d499f5c446359
Source dataset
uspto-grants-1999_10
Patent number
US05965745

Reaction notes

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