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Cesium carbonate → [5-(4H-Pyrazol-4-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanone

HRID 2068614
ノート
印刷プレビュー

反応式

HRID 2068614 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 10796Cesium carbonateHCID 177502781H-Pyrazole-4-boronic acidHCID 86646712HCID 86646712、化合物

生成物 1

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

試薬・触媒・溶媒 4

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒
HCID 962
Water
溶媒
HCID 80711,2-Dimethoxyethane溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-15450053dadb43349e5e0bfbe9f2667b
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08299063B2

反応ノート

読み込み中…

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