3,4-Dichlorobenzyl chloride → HCID 67279905, compound

HRID 1694377Notes

Reaction equation

HRID 1694377 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([NH:12][C:13]2([C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=3)[CH2:15][CH2:14]2)=[O:11])[CH2:3][CH2:2]1.[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:30]Cl.CCN(C(C)C)C(C)C>C(#N)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:30][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([NH:12][C:13]2([C:16]3[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=3)[CH2:14][CH2:15]2)=[O:11])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 81531DiisopropylethylamineHCID 58017568Methyl 4-(1-(indoline-7-carboxamido)cyclopropyl)benzoate

Product 1

HCID 67279905HCID 67279905, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 4-{1-[(2,3-dihydro-1H-indol-7-ylcarbonyl)amino]cyclopropyl}benzoate (110 mg, 0.327 mmol) was dissolved in acetonitrile (1.3 ml). 3,4-dichlorobenzyl chloride (136 ul. 0.981 mmol), DIPEA (171 ul, 0.981 mmol) and a crystal of TBAI were added. The mixture stirred at 70° C. for 2 h. The solvent was removed. Purification on silica gel.

Workup

  1. customThe solvent was removed
  2. customPurification on silica gel

Sources & evidence

ORD record
ord-fb2d5da43db0482c9200fd82dc129222
Source dataset
uspto-grants-2012_04
Patent number
US08158671B2

Reaction notes

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