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Sodium Bicarbonate → HCID 136166894、化合物

HRID 1617449
ノート
印刷プレビュー

反応式

HRID 1617449 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]/[C:10](/[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:11]\[OH:12])=[CH:4][CH:3]=1.[CH:25]1([B-](F)(F)F)[CH2:27][CH2:26]1.[K+].O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.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>[CH:25]1([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:9]/[C:10](/[C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:11]\[OH:12])=[CH:4][CH:3]=2)[CH2:27][CH2:26]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 4

HCID 516892Sodium BicarbonateHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 23697338Potassium cyclopropyltrifluoroborateHCID 136167080HCID 136167080、化合物

生成物 1

HCID 136166894HCID 136166894、化合物収率 49%

試薬・触媒・溶媒 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
触媒
HCID 962Water溶媒
HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of (E)-3-(4-bromo-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (example 5, 100 mg) in toluene (0.9 mL) and water (0.1 mL) was added potassium cyclopropyltrifluoroborate (47 mg), tri-potassium phosphate monohydrate (199 mg) and tetrakis(triphenylphosphine) palladium (0) (6 mg). The mixture was heated to 100° C. overnight. After cooling to rt a saturated aqueous solution of NaHCO3 was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1) to yield (E)-3-(4-cyclopropyl-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (43 mg, 49%) as a white foam, MS (ESI+): m/z=343.3 ([M+H]+).

後処理

  1. additionwas added
  2. customthe phases were separated
  3. extractionthe inorganic one was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1)

出典と根拠

ORDレコード
ord-c4f9373b47304128971d69706e5982b2
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08765730B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート