3,4-Dihydro-2H-1,4-benzoxazine → 4-[3-(dipyridin-3-ylmethoxy)pyridin-2-yl]-3,4-dihydro-2H-1,4-benzoxazine

HRID 1661135노트

반응식

HRID 1661135 반응식
Br[C:2]1[C:7]([O:8][CH:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[O:22]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[NH:25][CH2:24][CH2:23]1.CC(C)([O-])C.[Na+]>O1CCOCC1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[O:8][C:7]2[C:2]([N:25]3[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:22][CH2:23][CH2:24]3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=1

참가 물질

7

반응물 3

HCID 5850963,4-Dihydro-2H-1,4-benzoxazineHCID 23676156Sodium t-butoxideHCID 576132562-Bromo-3-(dipyridin-3-ylmethoxy)pyridine

생성물 1

HCID 247604044-[3-(dipyridin-3-ylmethoxy)pyridin-2-yl]-3,4-dihydro-2H-1,4-benzoxazine

시약·촉매·용매 3

HCID 178418851HCID 178418851, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 2-bromo-3-(dipyridin-3-ylmethoxy)pyridine (150 mg, 0.438 mmol) and 3,4-dihydro-2H-1,4-benzoxazine (59 mg, 0-438 mmol) in dry dioxane (5 mL) was added sodium t-butoxide (63 mg, 0.658 mmol), bis(tri-t-butylphosphine)palladium(0) (22 mg, 0.044 mmol). The mixture was heated to 100 C for 6 h. The reaction was cooled, diluted with water and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent evaporated. The residue was purified by silica gel chromatography (3-5% MeOH in CH2Cl2) to give 4-[3-(dipyridin-3-ylmethoxy)pyridin-2-yl]-3,4-dihydro-2H-1,4-benzoxazine (2-3). LRMS m/z (M+H) Calcd: 397.5, found: 397.1.

후처리

  1. temperatureThe mixture was heated to 100 C for 6 h
  2. temperatureThe reaction was cooled
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe residue was purified by silica gel chromatography (3-5% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-d07fc83a69804071ad984b97b48483a9
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030332B2

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