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Potassium Carbonate → 8-Chloroisoquinolin-3-amine

HRID 40662
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HRID 40662 반응식
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
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참가 물질

7

반응물 2

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

생성물 1

HCID 534190528-Chloroisoquinolin-3-amine수율 45.3%

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 263
1-Butanol
용매
2회
HCID 962Water용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c80f3624e34f46f0a3b2f0a31e7d1f15
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08530468B2

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