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

HRID 510978ノート

反応式

HRID 510978 の反応式
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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f6130e4ef57c4dc38ac59a44c666a420
出典データセット
uspto-grants-2015_08
特許番号
US09096600B2

反応ノート

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