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

HRID 1009632Notes

Reaction equation

HRID 1009632 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 1 Gb, 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-90b240e9636242b4832cf77441d09a8c
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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