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

HRID 1473643Notes

Reaction equation

HRID 1473643 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
40 °C

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-45a01ef9ed4a45d8b6539441cd632a8d
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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