Cyclopropanecarboxylic acid, 1-[4-amino-3-[2-(trimethylsilyl)ethynyl]phenyl]-, methyl ester → HCID 59129295, compound

HRID 1908373Notes

Reaction equation

HRID 1908373 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:15]#[C:16][Si](C)(C)C>CN(C=O)C.[Cu]I>[NH:1]1[C:2]2[C:3](=[CH:4][C:5]([C:8]3([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9]3)=[CH:6][CH:7]=2)[CH:15]=[CH:16]1

Participants

4

Reactant 1

HCID 59129467Cyclopropanecarboxylic acid, 1-[4-amino-3-[2-(trimethylsilyl)ethynyl]phenyl]-, methyl ester

Product 1

HCID 59129295HCID 59129295, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

To a degassed solution of methyl 1-(4-amino-3-((trimethylsilyl)ethynyl)phenyl)cyclopropanecarboxylate (4.69 g, 0.02 mol) in DMF (20 mL) was added CuI (1.5 g, 0.008 mol) under N2 at room temperature. The mixture was stirred for 3 hr at room temperature. The insoluble solid was filtered off and washed with EtOAc (50 mL×3). The filtrate was evaporated under reduced pressure to give a residue, which was purified by chromatography column on silica gel (petroleum ether/ethyl acetate=20:1) to give methyl 1-(1H-indol-5-yl)cyclopropanecarboxylate (2.2 g, 51%). 1H NMR (400 MHz, CDCl3) δ 7.61 (s, 1H), 7.33 (d, J=8.4 Hz, 1H), 7.23-7.18 (m, 2H), 6.52-6.51 (m, 1H) 3.62 (s, 3H), 1.65-1.62 (m, 2H), 1.29-1.23 (m, 2H).

Workup

  1. filtrationThe insoluble solid was filtered off
  2. washwashed with EtOAc (50 mL×3)
  3. customThe filtrate was evaporated under reduced pressure
  4. customto give a residue, which
  5. customwas purified by chromatography column on silica gel (petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-6aae2c6a6afb4a7b817132428f4dfd0f
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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