Potassium Carbonate → 4-(4-Bromo-2-fluoro-phenoxy)-6-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yloxy]-5-methyl-pyrimidine

HRID 1174780

반응식

HRID 1174780 반응식
Cl[C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]3[O:20][N:19]=[C:18]([CH:21]([CH3:23])[CH3:22])[N:17]=3)[CH2:12][CH2:11]2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([F:38])[CH:32]=1>CN(C=O)C>[Br:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][C:2]2[C:7]([CH3:8])=[C:6]([O:9][CH:10]3[CH2:15][CH2:14][N:13]([C:16]4[O:20][N:19]=[C:18]([CH:21]([CH3:23])[CH3:22])[N:17]=4)[CH2:12][CH2:11]3)[N:5]=[CH:4][N:3]=2)=[C:33]([F:38])[CH:32]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenolHCID 865973665-(4-(6-Chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole

생성물 1

HCID 598567634-(4-Bromo-2-fluoro-phenoxy)-6-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yloxy]-5-methyl-pyrimidine수율 48%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

A mixture of 4-chloro-6-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yloxy]-5-methyl-pyrimidine (1.51 g, 4.46 mmol), potassium carbonate (1.25 g, 9.03 mmol), and 4-bromo-2-fluorophenol (1.11 g, 5.82 mmol) in 15 mL DMF was heated in microwave for 1 hour at 150° C. The mixture was purified by column chromatography on silica gel with hexane/ethyl acetate (3:1 v/v) to give Compound C40 as an oil (1.05 g, 48%). 1H NMR (CDCl3, 400 MHz) δ 1.20-1.22 (d, 6H), 1.83-1.91 (m, 2H), 1.98-2.05 (m, 2H), 2.11 (s, 3H), 2.77-2.87 (m, 1H), 3.53-3.59 (m, 2H), 3.74-3.80 (m, 2H), 5.31-5.36 (m, 1H), 6.99-7.03 (m, 1H), 7.22-7.29 (m, 2H), 8.13 (s, 1H). Exact mass calculated for C21H23BrFN5O3 491.1, found 492.4 (MH+).

후처리

  1. customThe mixture was purified by column chromatography on silica gel with hexane/ethyl acetate (3:1 v/v)

출처 및 근거

ORD 기록
ord-a4259290f5104ce1b8cd7d58fe101eb8
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838525B2

연결된 노트

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