Dichloromethane → [6-(Dimethylcarbamoyl)pyridin-3-yl]boronic acid

HRID 510978노트

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HRID 510978 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[N:6][CH:7]=1.CC1(C)C(C)(C)[O:17][B:16](B2OC(C)(C)C(C)(C)O2)[O:15]1.ClCCl.C([O-])(=O)C.[K+]>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].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]>[CH3:11][N:10]([CH3:12])[C:8]([C:5]1[N:6]=[CH:7][C:2]([B:16]([OH:17])[OH:15])=[CH:3][CH:4]=1)=[O:9]

참가 물질

9

반응물 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 228316185-bromo-N,N-dimethylpicolinamide

생성물 1

HCID 53438177[6-(Dimethylcarbamoyl)pyridin-3-yl]boronic acid수율 52.6%

시약·촉매·용매 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

A mixture of 5-bromo-N,N-dimethylpyridine-2-carboxamide (23 g, 98 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2]bi[[1,3,2]dioxaborolanyl] (27 g, 110 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (4.8 g, 5.9 mmol), 1,1′-bis(diphenylphosphino)ferrocene (3.3 g, 5.9 mmol), and potassium acetate (30 g, 300 mmol) in 1,4-dioxane (600 mL) was heated at 120° C. for 16 h. The mixture was cooled to rt and diluted with EtOAc. The organic solution was washed with saturated ammonium chloride solution which was discarded and then with water (1 L). The water wash was evaporated to give the desired compound (10 g, 50%). LCMS calculated for C8H12BN2O3 (M+H)+: m/z=195.1. found: 195.1.

후처리

  1. temperatureThe mixture was cooled to rt
  2. washThe organic solution was washed with saturated ammonium chloride solution which
  3. washThe water wash
  4. customwas evaporated

출처 및 근거

ORD 기록
ord-f6130e4ef57c4dc38ac59a44c666a420
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096600B2

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