Diisopropylethylamine → Methyl 2-(4-methyl-2-(piperidin-1-yl)-6-(quinolin-5-yl)pyrimidin-5-yl)pentanoate

HRID 1399707

반응식

HRID 1399707 반응식
Cl[C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:16])[N:5]=[C:4]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:3]=1.C(N(CC)C(C)C)(C)C.[N:32]1[C:41]2[C:36](=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:16][C:6]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:2]([C:37]2[CH:38]=[CH:39][CH:40]=[C:41]3[C:36]=2[CH:35]=[CH:34][CH:33]=[N:32]3)[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:5]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 5153389Quinoline-5-boronic acidHCID 86665653Methyl 2-(4-chloro-6-methyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate

생성물 1

HCID 50995731Methyl 2-(4-methyl-2-(piperidin-1-yl)-6-(quinolin-5-yl)pyrimidin-5-yl)pentanoate수율 67%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 18180031Water 1,2-dimethoxyethane용매

실험 절차

This compound was prepared according to general method E from methyl 2-(4-chloro-6-methyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate (0.081 g; 0.25 mmol), tetrakis(triphenylphosphine) palladium(0) (0.029 g; 0.025 mmol), N,N-diisopropylethylamine (0.172 mL; 1.00 mmol) and quinolin-5-ylboronic acid (0.086 g; 0.500 mmol) in DME-water (1 mL) for 20 min. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane furnished 0.070 g (67%) of the title compound.

후처리

  1. customThis compound was prepared
  2. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane

출처 및 근거

ORD 기록
ord-574190ea41b140d8b9c55f307df8ca2e
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906906B2

연결된 노트

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