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碳酸氢铯 → [5-(4H-Pyrazol-4-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanone

HRID 2068614
笔记
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反应方程式

HRID 2068614 反应方程式
Br[C:2]1[S:6][CH:5]=[C:4]([C:7]([N:9]2[C@@H:18]3[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11][CH2:10]2)=[O:8])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:25]1[CH:29]=[C:28](B(O)O)[CH:27]=[N:26]1>COCCOC.O.C(OCC)(=O)C.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.[Pd]>[N:25]1[N:26]=[CH:27][CH:28]([C:2]2[S:6][CH:5]=[C:4]([C:7]([N:9]3[CH:18]4[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]4)[CH2:12][CH2:11][CH2:10]3)=[O:8])[CH:3]=2)[CH:29]=1
参与物反应条件实验过程后处理来源与证据反应笔记

参与物

8

反应物 3

HCID 10796碳酸氢铯HCID 177502781H-吡唑-4-硼酸HCID 86646712HCID 86646712,化合物

产物 1

HCID 44224461[5-(4H-Pyrazol-4-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanone收率 21.1%

试剂、催化剂与溶剂 4

HCID 11979704四三苯基膦钯催化剂
HCID 962
聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]
溶剂
HCID 8071乙二醇二甲醚溶剂
HCID 8857乙酸乙酯溶剂

反应条件

温度
140 °C

实验过程

cis-(5-Bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone (0.15 mmol) was added to a solution of caesium carbonate (0.15 mmol), 4-pyrazoleboronic acid (0.3 mmol) and palladium tetrakis(triphenylphosphine) (0.03 mmol) in DME (6 mL), IMS (2 mL) and water (0.001 mL). The reaction mixture was heated by microwave irradiation to 140° C. for 20 minutes and then diluted with ethyl acetate (5 mL) and washed with water. The organic solution was dried and filtered and the solvent evaporated. The residue was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum to give the title compound as a pale yellow oil (10 mg). LCMS m/z 316.27 [M+H]+ RT=9.34 min. (Analytical Method 2).

后处理

  1. washwashed with water
  2. customThe organic solution was dried
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe residue was purified by HPLC
  6. washeluting with 10%-98% acetonitrile in water (0.1% formic acid) over 30 minutes
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

来源与证据

ORD记录
ord-15450053dadb43349e5e0bfbe9f2667b
来源数据集
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
专利号
US08299063B2

反应笔记

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本页导航参与物反应条件实验过程后处理来源与证据反应笔记