Water → N-[4-(3-cyano-6-ethoxy-1-ethyl-indol-2-yl)phenyl]cyclopropanecarboxamide

HRID 506102Notes

Reaction equation

HRID 506102 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:22][CH3:23])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=3)=[CH:4][CH:3]=1.CCN(CC)CC.[CH:31]1([C:34](Cl)=[O:35])[CH2:33][CH2:32]1.O>C1COCC1.C(OCC)(=O)C>[C:17]([C:16]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH2:20][CH3:21])=[CH:13][CH:14]=2)[N:9]([CH2:22][CH3:23])[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:34]([CH:31]2[CH2:33][CH2:32]2)=[O:35])=[CH:7][CH:6]=1)#[N:18]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 594252742-(4-aminophenyl)-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile

Product 1

HCID 25052168N-[4-(3-cyano-6-ethoxy-1-ethyl-indol-2-yl)phenyl]cyclopropanecarboxamideYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 2-(4-aminophenyl)-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile (3.66 g, 12 mmol), prepared as described in example 1Gb, in 20 mL of THF is added Et3N (3.37 ml) and cyclopropanecarbonyl chloride (1.6 mL, 18 mmol). The mixture is stirred for 3 h at room temperature. Then water and ethyl acetate are added to the reaction mixture. The organic layer is separated, washed with brine (2×), dried over anhydrous Na2SO4, filtered and concentrated. The residue is recrystallized with ethyl acetate and hexane to yield 99% of cyclopropanecarboxylic acid [4-(3-cyano-6-ethoxy-1-ethyl-1H-indol-2-yl)-phenyl]-amide.

Workup

  1. customThe organic layer is separated
  2. washwashed with brine (2×)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is recrystallized with ethyl acetate and hexane

Sources & evidence

ORD record
ord-ad6fa9c9e2ff4ec69b6870226fc0e07f
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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