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Potassium Carbonate → 8-Chloroisoquinolin-3-amine

HRID 40662
ノート
印刷プレビュー

反応式

HRID 40662 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Cl:12])[CH:5]=[C:4]([NH:13]C(=O)C)[N:3]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH:2]=[N:3][C:4]([NH2:13])=[CH:5]2
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

7

反応物 2

HCID 11430Potassium CarbonateHCID 59636331N-(1-bromo-8-chloroisoquinolin-3-yl)acetamide

生成物 1

HCID 534190528-Chloroisoquinolin-3-amine収率 45.3%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 263
1-Butanol
溶媒
2 回
HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

N-(1-Bromo-8-chloroisoquinolin-3-yl)acetamide (1.00 g, 3.33 mmol), potassium carbonate (0.508 mg, 3.67 mmol), triphenylphosphine (35 mg, 0.134 mmol) and palladium acetate (7.49 mg, 0.033 mmol) were stirred in 1-butanol (10 mL) with nitrogen bubbling through it for 10 minutes. Butanol (5 mL) was added to the reaction mixture, which was then heated overnight at 100° C. in a sealed vial. The reaction mixture was cooled, diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to give an orange solid. Flash chromatography on silica (20 g), eluting with 15-60% ethyl acetate-hexane, gave the title compound as a yellow solid (333 mg, 1.51 mmol, 45%). LC-MS (1) Rt=1.68 min; m/z (ES+) 221/223.

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give an orange solid
  7. washFlash chromatography on silica (20 g), eluting with 15-60% ethyl acetate-hexane

出典と根拠

ORDレコード
ord-c80f3624e34f46f0a3b2f0a31e7d1f15
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08530468B2

反応ノート

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