Ethyl 5-Bromoindole-2-carboxylate → HCID 67395583, compound

HRID 1023733Notes

Reaction equation

HRID 1023733 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([NH2:14])=[O:13])[O:7][C:8]=1[CH:9]([CH3:11])[CH3:10])([CH3:3])[CH3:2].Br[C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19]2>>[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([NH:14][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19]3)=[O:13])[O:7][C:8]=1[CH:9]([CH3:10])[CH3:11])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 259091Ethyl 5-Bromoindole-2-carboxylateHCID 58420521HCID 58420521, compound

Product 1

HCID 67395583HCID 67395583, compoundYield 32.3%

Procedure

In the same manner as that of Example 32, 4,5-diisopropylfuran-2-carboxamide (71 mg, 0.364 mmol) and ethyl 5-bromoindole-2-carboxylate (195 mg, 0.728 mmol) were coupled. The reaction mixture was treated in a conventional manner, and the resultant was purified by silica gel chromatography [hexane-ethyl acetate (4:1), and 1% methanol-chloroform] and then recrystallized to obtain ethyl 5-[(4,5-diisopropylfuran-2-carbonyl)amino]-2-indolecarboxylate (45 mg, 32%) as colorless prisms, together with the collected starting material (39 mg, 55%).

Workup

  1. additionThe reaction mixture was treated in a conventional manner
  2. customthe resultant was purified by silica gel chromatography [hexane-ethyl acetate (4:1), and 1% methanol-chloroform]
  3. customrecrystallized

Sources & evidence

ORD record
ord-5442dc53d52e4c04a8adfa24f16fd73a
Source dataset
uspto-grants-2014_05
Patent number
US08722730B2

Reaction notes

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