Diisopropylethylamine → 2-[(2S)-2-(3-bromo-7-oxo-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 339984노트

반응식

HRID 339984 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:12]Br)[C:5]([C:8]([O:10]C)=O)=[N:6][CH:7]=1.[NH2:14][C@@H:15]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=1)[CH2:16][N:17]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]1=[O:27].C(N(CC)C(C)C)(C)C>C(O)CCC>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][N:14]([C@@H:15]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=3)[CH2:16][N:17]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]3=[O:27])[C:8](=[O:10])[C:5]2=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 58171990Methyl 5-bromo-3-(bromomethyl)pyridine-2-carboxylateHCID 58226866(S)-2-(2-amino-3-(3-fluorophenyl)propyl)isoindoline-1,3-dione

생성물 1

HCID 866814722-[(2S)-2-(3-bromo-7-oxo-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione수율 61%

시약·촉매·용매 1

HCID 2631-Butanol용매

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온도
120 °C

실험 절차

A mixture of methyl 5-bromo-3-(bromomethyl)pyridine-2-carboxylate (500.0 mg, 1.618 mmol), 2-[(2S)-2-amino-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione (482.8 mg, 1.618 mmol) and N,N-diisopropylethylamine (0.564 mL, 3.24 mmol) in 1-butanol (10.0 mL) was stirred at 120° C. for 2 h under microwave. Purification by combi-flash chromatography gave 0.48 g (61% yield) of the desired product. LC-MS found: 494.1 (M+H)+.

후처리

  1. customPurification by combi-flash chromatography

출처 및 근거

ORD 기록
ord-5ad24e34587d4603acccd651ca008567
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895571B2

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