Ethanamine, 2-fluoro-, hydrochloride → 4-Chloro-7-{1-(tert-butoxycarbonyl)-5-[(2-fluoroethyl)aminomethyl]indol-2-yl}isoindolinone

HRID 21050

Reaction equation

HRID 21050 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH:20]=O)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29].Cl.[F:31][CH2:32][CH2:33][NH2:34].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][NH:34][CH2:33][CH2:32][F:31])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29]

Participants

5

Reactant 3

HCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Product 1

HCID 866282284-Chloro-7-{1-(tert-butoxycarbonyl)-5-[(2-fluoroethyl)aminomethyl]indol-2-yl}isoindolinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Step 1 of Example 56, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (20.0 mg, 0.0487 mmol) was dissolved in dichloromethane (0.5 mL). The solution was treated with 2-fluoroethylamine hydrochloride (20 mg, 0.20 mmol) and sodium triacetoxyborohydride (32 mg, 0.15 mmol) to obtain 4-chloro-7-{1-(tert-butoxycarbonyl)-5-[(2-fluoroethyl)aminomethyl]indol-2-yl}isoindolinone.

Sources & evidence

ORD record
ord-bc2e9bba57144aaa80460cf22207043d
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

Loading…