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Water → HCID 73774720, compound

HRID 2207283
Notes
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Reaction equation

HRID 2207283 reaction equation
[Cl:1][C:2]1[C:3]([O:18][C:19]2[CH:20]=[N:21][C:22](Cl)=[CH:23][C:24]=2[C:25]2[N:29]([CH3:30])[N:28]=[CH:27][CH:26]=2)=[CH:4][C:5]([F:17])=[C:6]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])[CH:7]=1.[F:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1.C([O-])([O-])=O.[Na+].[Na+].O>CN(C)C=O.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:1][C:2]1[C:3]([O:18][C:19]2[CH:20]=[N:21][C:22]([C:37]3[CH:36]=[CH:35][CH:34]=[C:33]([F:32])[CH:38]=3)=[CH:23][C:24]=2[C:25]2[N:29]([CH3:30])[N:28]=[CH:27][CH:26]=2)=[CH:4][C:5]([F:17])=[C:6]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 90100720HCID 90100720, compound

Product 1

HCID 73774720HCID 73774720, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

10 mg (0.02 mmol) of 5-chloro-4-((6-chloro-4-(1-methyl-1H-pyrazol-5-yl)pyridin-3-yl)oxy)-2-fluoro-N-(thiazol-2-yl)benzenesulfonamide was dissolved in 3 mL of N,N-dimethylformamide, and 4.2 mg (0.03 mmol) of (3-fluorophenyl)boronic acid was added thereto, and then 2.3 mg (10 mol %) of Pd(PPh3)4, 6.3 mg (0.6 mmol) of Na2CO3, and 1 mL of H2O were added thereto. After reacting with microwave reactor at 120° C. for 10 minutes, the solvent was removed, and the remaining material was diluted with ethyl acetate and the organic layer was separated, and washed with saturated sodium chloride. The organic layer was collected, dried with magnesium sulfate to remove water, and concentrated under reduced pressure, and the residue was purified by column chromatography (developing solvent, hexane:ethyl acetate=3:1) to obtain 4 mg (36% yield) of the title compound.

Workup

  1. customthe solvent was removed
  2. additionthe remaining material was diluted with ethyl acetate
  3. customthe organic layer was separated
  4. washwashed with saturated sodium chloride
  5. customThe organic layer was collected
  6. dry with materialdried with magnesium sulfate
  7. customto remove water
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was purified by column chromatography (developing solvent, hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-b06b83bc9ee142418faaf124c0ec2921
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09376429B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes