Cyclopropanecarbonyl chloride → HCID 69665353, compound

HRID 1828997Notes

Reaction equation

HRID 1828997 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:20])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH:30]1([C:33](Cl)=[O:34])[CH2:32][CH2:31]1>C1COCC1>[O:20]=[C:12]1[C:11](=[C:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:33]([CH:30]4[CH2:32][CH2:31]4)=[O:34])[CH:10]=3)[CH2:6][O:7]2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13]1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 696591993-(6-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 69665353HCID 69665353, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(6-Amino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (50.0 mg, 0.189 mmol) and N,N-diisopropylethylamine (98.8 μL, 0.567 mmol) in 2.0 mL THF was added cyclopropane carbonyl chloride (17.2 μL, 0.189 mmol). After stirring at room temperature for 1 h, the slurry was warmed briefly, stirred 10 min at room temperature, filtered and rinsed with MeOH and EtOAc/hexanes (1:1) to afford the title compound (44.7 mg, 71%) as a yellow solid.

Workup

  1. temperaturethe slurry was warmed briefly
  2. stirringstirred 10 min at room temperature
  3. filtrationfiltered
  4. washrinsed with MeOH and EtOAc/hexanes (1:1)

Sources & evidence

ORD record
ord-5b781913479248bba6a241b51590c6c7
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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