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Water → HCID 73776714, compound

HRID 2207279
Notes
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Reaction equation

HRID 2207279 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]3[S:20][CH:21]=[CH:22][N:23]=3)(=[O:17])=[O:16])=[CH:11][C:10]=2[C:24]#[N:25])=[C:4]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH:3]=1.[F:32][C:33]1[C:38](B(O)O)=[CH:37][CH:36]=[C:35]([F:42])[N:34]=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>[C:24]([C:10]1[CH:11]=[C:12]([S:15]([NH:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)(=[O:17])=[O:16])[CH:13]=[CH:14][C:9]=1[O:8][C:5]1[C:4]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[CH:3][C:2]([C:38]2[C:33]([F:32])=[N:34][C:35]([F:42])=[CH:36][CH:37]=2)=[N:7][CH:6]=1)#[N:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2762713(2,6-Difluoropyridin-3-yl)boronic acidHCID 901006214-((6-chloro-[4,4'-bipyridin]-3-yl)oxy)-3-cyano-N-(thiazol-2-yl)benzenesulfonamide

Product 1

HCID 73776714HCID 73776714, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 6228DimethylformamideSolvent

Procedure

10 mg (0.02 mmol) of 4-((6-chloro-[4,4′-bipyridin]-3-yl)oxy)-3-cyano-N-(thiazol-2-yl)benzenesulfonamide was dissolved in 3 mL of N,N-dimethylformamide, and 5 mg (0.03 mmol) of (2,6-difluoropyridin-3-yl)boronic acid was added thereto, and then 2.4 mg (10 mol %) of Pd(PPh3)4, 6.7 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 2 mg (19% 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-7f948e6144904a3cb34ddc57fea6867b
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