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Water → HCID 57751037, 화합물

HRID 2283311
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HRID 2283311 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

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

생성물 1

HCID 57751037HCID 57751037, 화합물수율 19%

시약·촉매·용매 4

HCID 178418807
HCID 178418807, 화합물
촉매
HCID 6344Dichloromethane용매
HCID 8028Tetrahydrofuran용매
HCID 57417360Sodium chloride; water용매

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온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d4a2b1649e4c4b889da0e726262d60ab
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09145380B2

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