Potassium Carbonate → 5-((2'-Methyl-[2,4'-bipyridin]-4-yl)oxy)pyridin-2-amine

HRID 1049243노트

반응식

HRID 1049243 반응식
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:22][C:23]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[CH:25][N:24]=1>O1CCOCC1.O.CCOC(C)=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>[CH3:22][C:23]1[CH:28]=[C:27]([C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=3)[CH:5]=[CH:4][N:3]=2)[CH:26]=[CH:25][N:24]=1

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 164142742-Methylpyridine-4-boronic acid pinacol esterHCID 593227885-(2-Chloropyridin-4-yloxy)pyridin-2-amine

생성물 1

HCID 904032625-((2'-Methyl-[2,4'-bipyridin]-4-yl)oxy)pyridin-2-amine수율 89%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

A solution of Example A9 (0.440 g, 1.985 mmol) in dioxane (8 mL) was sparged with Ar, treated with a solution of K2CO3 (0.549 g, 3.97 mmol) in water (2 mL) and 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.565 g, 2.58 mmol), sparged again with Ar, treated with Pd(PPh3)4 (0.229 g, 0.199 mmol) and heated at 80° C. overnight. The mixture was cooled to RT, diluted with EtOAc, the solids removed via filtration through diatomaceous earth and the filtrate concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 5-((2′-methyl-[2,4′-bipyridin]-4-yl)oxy)pyridin-2-amine (490 mg, 89%) as a light brown solid. MS (ESI) m/z: 279.2 (M+H+).

후처리

  1. customsparged again with Ar
  2. temperatureThe mixture was cooled to RT
  3. customthe solids removed via filtration through diatomaceous earth
  4. concentrationthe filtrate concentrated to dryness
  5. custompurified via silica gel chromatography (MeOH/DCM)

출처 및 근거

ORD 기록
ord-c47bfd910b2c4d40971ac243810182b1
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382228B2

반응 노트

불러오는 중…