Water → HCID 68491573, compound

HRID 1038758Notes

Reaction equation

HRID 1038758 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][N:17]=3)[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:2].C(N(CC)CC)C.[Cl:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[Cl:41])[C:35](Cl)=[O:36].O>C1COCC1>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:35](=[O:36])[C:34]4[CH:38]=[CH:39][C:40]([Cl:41])=[C:32]([Cl:31])[CH:33]=4)=[CH:18][N:17]=3)[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 68496504HCID 68496504, compound

Product 1

HCID 68491573HCID 68491573, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[4-(5-Aminopyridin-2-yloxy)indole-1-yl]acetic acid ethyl ester (0.715 g, 2.30 mmol) was dissolved in THF (10 mL). To the solution were added triethylamine (0.320 mL, 2.30 mmol), then 3,4-Dichlorobenzoyl chloride (0.481 g, 2.30 mmol), and the resulting solution was stirred for 30 minutes at room temperature. Water (50 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (50 mL). After the organic layer was washed with brine, then dried over anhydrous sodium sulfate, the solvent was evaporated. The obtained residue was recrystallized from ethyl acetate and n-hexane to yield 0.972 g of the title compound as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 mL)
  2. washAfter the organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customThe obtained residue was recrystallized from ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-d8bea8ccabe142aa9a7ecc4f72707899
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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