Water → HCID 73775013, compound

HRID 2207290Notes

Reaction equation

HRID 2207290 reaction equation
C(OC(=O)[N:7]([S:13]([C:16]1[CH:21]=[C:20]([Cl:22])[C:19]([O:23][C:24]2[CH:25]=[N:26][C:27](Cl)=[CH:28][C:29]=2[C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[CH:18][C:17]=1[F:37])(=[O:15])=[O:14])[C:8]1[S:9][CH:10]=[CH:11][N:12]=1)(C)(C)C.[F:39][C:40]1[CH:41]=[C:42](B(O)O)[CH:43]=[CH:44][CH:45]=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:22][C:20]1[C:19]([O:23][C:24]2[CH:25]=[N:26][C:27]([C:44]3[CH:43]=[CH:42][CH:41]=[C:40]([F:39])[CH:45]=3)=[CH:28][C:29]=2[C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[CH:18][C:17]([F:37])=[C:16]([S:13]([NH:7][C:8]2[S:9][CH:10]=[CH:11][N:12]=2)(=[O:15])=[O:14])[CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 118522215HCID 118522215, compound

Product 1

HCID 73775013HCID 73775013, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

20 mg (0.03 mmol) of tert-butyl((5-chloro-4-((6′-chloro-[3,4′-bipyridin]-3′-yl)oxy)-2-fluorophenyl)sulfonyl)(thiazol-2-yl)carbamate was dissolved in 3 mL of N,N-dimethylformamide, and 7 mg (0.05 mmol) of (3-fluorophenyl)boronic acid was added thereto, and then 3.8 mg (10 mol %) of Pd(PPh3)4, 10.6 mg (0.10 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 5 mg (27% 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-c3eb254d18e844e4aec4b64edc53e95a
Source dataset
uspto-grants-2016_06
Patent number
US09376429B2

Reaction notes

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