Potassium Carbonate → Perfluorophenyl 1-(5,6-dichloro-2-methoxypyridin-3-yl)isoquinoline-6-sulfonate

HRID 1473643노트

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HRID 1473643 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([O:15][C:16]3[C:21]([F:22])=[C:20]([F:23])[C:19]([F:24])=[C:18]([F:25])[C:17]=3[F:26])(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Cl:27][C:28]1[CH:29]=[C:30](B(O)O)[C:31]([O:35][CH3:36])=[N:32][C:33]=1[Cl:34].C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:27][C:28]1[CH:29]=[C:30]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([S:12]([O:15][C:16]4[C:21]([F:22])=[C:20]([F:23])[C:19]([F:24])=[C:18]([F:25])[C:17]=4[F:26])(=[O:14])=[O:13])=[CH:9][CH:10]=3)[CH:5]=[CH:4][N:3]=2)[C:31]([O:35][CH3:36])=[N:32][C:33]=1[Cl:34]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 86687382Perfluorophenyl 1-chloroisoquinoline-6-sulfonateHCID 86687715HCID 86687715, 화합물

생성물 1

HCID 86687714Perfluorophenyl 1-(5,6-dichloro-2-methoxypyridin-3-yl)isoquinoline-6-sulfonate

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

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온도
40 °C

실험 절차

A vial was charged with perfluorophenyl 1-chloroisoquinoline-6-sulfonate (From Step 1 in Example 73; 0.050 g, 0.122 mmol), (5,6-dichloro-2-methoxypyridin-3-yl)boronic acid (0.030 g, 0.134 mmol), potassium carbonate (0.051 g, 0.366 mmol), and Pd(Ph3P)4 (0.014 g, 0.012 mmol). The vial was flushed with Ar (g), then dioxane (0.915 ml) and water (0.305 ml) were added. The reaction was heated at 40° C. for one hour. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 12 g, gradient elution 0-50% EtOAc:Heptane) to afford perfluorophenyl 1-(5,6-dichloro-2-methoxypyridin-3-yl)isoquinoline-6-sulfonate as a white solid. (ESI) 551.0 (M+H)+.

후처리

  1. customThe vial was flushed with Ar (g)
  2. additiondioxane (0.915 ml) and water (0.305 ml) were added
  3. additionThe reaction was diluted with ethyl acetate
  4. washwashed with water
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialthe combined organic layers were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe material was purified via column chromatography (RediSep Gold 12 g, gradient elution 0-50% EtOAc:Heptane)

출처 및 근거

ORD 기록
ord-45a01ef9ed4a45d8b6539441cd632a8d
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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