Acetic Acid → 4-Chloro-7-(1-(tert-butoxycarbonyl)-5-[(2-hydroxyethyl)aminomethyl]indol-2-yl)isoindolinone

HRID 21016

반응식

HRID 21016 반응식
[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].[NH2:30][CH2:31][CH2:32][OH:33].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][NH:30][CH2:31][CH2:32][OH:33])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 700EthanolamineHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

생성물 1

HCID 684934874-Chloro-7-(1-(tert-butoxycarbonyl)-5-[(2-hydroxyethyl)aminomethyl]indol-2-yl)isoindolinone수율 88.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (40.0 mg, 0.0974 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with 2-aminoethanol (0.024 mL, 0.39 mmol), acetic acid (0.112 mL, 1.96 mmol) and sodium triacetoxyborohydride (103 mg, 0.486 mmol), followed by purification by preparative thin-layer chromatography (hexane/ethyl acetate=1/2) to obtain 4-chloro-7-(1-(tert-butoxycarbonyl)-5-[(2-hydroxyethyl)aminomethyl]indol-2-yl)isoindolinone (39.4 mg, yield 871).

후처리

  1. customfollowed by purification by preparative thin-layer chromatography (hexane/ethyl acetate=1/2)

출처 및 근거

ORD 기록
ord-73bf989f857b4d09be8e831772c26208
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

연결된 노트

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