Sodium Carbonate → HCID 73776717, compound

HRID 2207281Notes

Reaction equation

HRID 2207281 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:34]=[CH:33][O:32][CH:31]=2)=[CH:18][C:17]=1[F:36])(=[O:15])=[O:14])[C:8]1[N:9]=[CH:10][S:11][CH:12]=1)(C)(C)C.[F:38][C:39]1[C:44](B(O)O)=[CH:43][CH:42]=[CH:41][N:40]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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[C:29]([C:30]3[CH:34]=[CH:33][O:32][CH:31]=3)=[CH:28][C:27]([C:44]3[C:39]([F:38])=[N:40][CH:41]=[CH:42][CH:43]=3)=[N:26][CH:25]=2)=[CH:18][C:17]([F:36])=[C:16]([S:13]([NH:7][C:8]2[N:9]=[CH:10][S:11][CH:12]=2)(=[O:15])=[O:14])[CH:21]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 118522192HCID 118522192, compound

Product 1

HCID 73776717HCID 73776717, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

10 mg of tert-butyl((5-chloro-4-((6-chloro-4-(furan-3-yl)pyridin-3-yl)oxy)-2-fluorophenyl)sulfonyl)(thiazol-4-yl)carbamate was dissolved in 1,4-dioxane/H2O=1:1 (0.38 mL), and 3.5 mg of (2-fluoropyridin-3-yl)boronic acid, 0.65 mg (3 mol %) of Pd(PPh3)4 and 5.96 mg of Na2CO3 were added thereto. After reacting with microwave reactor at 120° C. for 5 minutes, 1,4-dioxane was removed by concentrating under reduced pressure. After extracting with ethyl acetate, the extract was treated with MgSO4, and concentrated under reduced pressure. The residue was separated by PLC (developing solvent, EA:n-Hex=1:1) to obtain 6.7 mg (72% yield) of the title compound.

Workup

  1. additionwere added
  2. custom1,4-dioxane was removed
  3. concentrationby concentrating under reduced pressure
  4. extractionAfter extracting with ethyl acetate
  5. additionthe extract was treated with MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated by PLC (developing solvent, EA:n-Hex=1:1)

Sources & evidence

ORD record
ord-22663b0265ee4a31a92b5d833df004de
Source dataset
uspto-grants-2016_06
Patent number
US09376429B2

Reaction notes

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