Cesium fluoride → 3-Pyridazin-4-ylbiphenyl-4-ol

HRID 1619624노트

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HRID 1619624 반응식
I[C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C([Sn](CCCC)(CCCC)[C:20]1[CH:25]=[CH:24][N:23]=[N:22][CH:21]=1)CCC.[F-].[Cs+]>C(#N)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu](I)I>[N:22]1[CH:21]=[CH:20][C:25]([C:2]2[CH:3]=[C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:5]=[CH:6][C:7]=2[OH:8])=[CH:24][N:23]=1

참가 물질

7

반응물 3

HCID 25953Cesium fluorideHCID 41061404-Hydroxy-3-iodobiphenylHCID 64097334-(Tributylstannyl)pyridazine

생성물 1

HCID 1362008863-Pyridazin-4-ylbiphenyl-4-ol수율 32%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6342Acetonitrile용매

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온도
45 °C

실험 절차

3-Iodobiphenyl-4-ol (1 g, 3.4 mmol) was mixed with 4-(tributylstannyl)pyridazine (1.25 g 3.4 mmol), caesium fluoride (1.03 g 6.8 mmol), tetrakis(triphenylphosphine) palladium (0) (195 mg, 0.17 mmol) and copper iodide (128 mg 0.68 mmol) in acetonitrile (10 mL). The reaction was degassed 3 times before being placed under nitrogen and heated to 45° C. for 16 hours. The reaction was diluted with acetonitrile (20 mL), washed with heptane (2×20 mL) then absorbed onto silica and purified by silica gel column chromatography (ISCO™, 40 g, 50%-100% ethyl acetate in heptane gradient elution) to afford the title compound (270 mg, 32%) as a pale yellow solid.

후처리

  1. customThe reaction was degassed 3 times
  2. additionThe reaction was diluted with acetonitrile (20 mL)
  3. washwashed with heptane (2×20 mL)
  4. customthen absorbed onto silica
  5. custompurified by silica gel column chromatography (ISCO™, 40 g, 50%-100% ethyl acetate in heptane gradient elution)

출처 및 근거

ORD 기록
ord-20595fd2e1be40208b9753ad19243e68
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772293B2

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