Water → HCID 57751037, compound

HRID 2283311Notes

Reaction equation

HRID 2283311 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[CH:5][CH:4]=1.Br[C:19]1[CH:20]=[C:21]([S:25]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[S:35]([NH2:38])(=[O:37])=[O:36])(=[O:27])=[O:26])[CH:22]=[CH:23][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1COCC1.[Cl-].[Na+].O.C(Cl)Cl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:19]2[CH:20]=[C:21]([S:25]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[S:35](=[O:36])(=[O:37])[NH2:38])(=[O:26])=[O:27])[CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 177505082-Methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 57751032HCID 57751032, compound

Product 1

HCID 57751037HCID 57751037, compoundYield 19%

Reagents, catalysts & solvents 4

HCID 178418807HCID 178418807, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
120 °C

Procedure

1,1′-Bis(diphenylphosphino)ferrocene palladium dichloride methylene chloride adduct (14 mg, 0.02 mmol) was added to a solution of 6-methoxy pyridine-2-boronic acid pinacol ester (135 mg, 0.57 mmol), 2-[(3-bromophenyl)sulfonylamino]benzenesulfonamide (150 mg, 0.38 mmol) (see Example 113a) and Na2CO3 (0.18 mg, 1.72 mmol) in THF:water, 10:1 (4 mL). The reaction mixture was heated in a microwave reactor at 120° C. for 20 min. Some DCM was added followed by brine and the aqueous layer was extracted twice with DCM. The combined organic layers were dried with Na2SO4 and after filtration and evaporation the crude was purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer) to give the title compound (30 mg, 19%) as a yellow oil.

Workup

  1. extractionthe aqueous layer was extracted twice with DCM
  2. dry with materialThe combined organic layers were dried with Na2SO4
  3. filtrationafter filtration and evaporation the crude
  4. customwas purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer)

Sources & evidence

ORD record
ord-d4a2b1649e4c4b889da0e726262d60ab
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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