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2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 3,4-bis(Benzyloxy)-6-[(4-fluorophenyl)methyl]pyridazine

HRID 927102
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HRID 927102 반응식
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12](Cl)=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[Br-].[F:59][C:60]1[CH:67]=[CH:66][C:63]([CH2:64][Zn+])=[CH:62][CH:61]=1>O1CCCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([CH2:64][C:63]2[CH:66]=[CH:67][C:60]([F:59])=[CH:61][CH:62]=2)=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

7

반응물 3

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 122134743,4-Bis(benzyloxy)-6-chloropyridazine2회HCID 178505763HCID 178505763, 화합물

생성물 1

HCID 712704273,4-bis(Benzyloxy)-6-[(4-fluorophenyl)methyl]pyridazine수율 97%

시약·촉매·용매 3

HCID 167845palladium(II) acetate
촉매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

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온도
65 °C

실험 절차

To a solution of 3,4-bis(benzyloxy)-6-chloropyridazine (Intermediate 1) (1 g, 3.06 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.117 g, 0.245 mmol) and palladium (II) acetate (0.027 g, 0.122 mmol) in tetrahydrofuran (6.12 ml) under nitrogen was added (4-fluorobenzyl)zinc(II) bromide (9.18 ml, 4.59 mmol) and the resulting red/brown mixture was heated at 65° C. for 24 hours. The reaction mixture was cooled, diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution, saturated ammonium chloride solution and brine. The organics were dried (MgSO4), filtered and solvent removed in vacuo to give a brown oil. The oil was purified by silica chromatography (eluting with 0-100% ethyl acetate in petrol) to yield the title compound (663 mg, 1.61 mmol, 97% yield).

후처리

  1. temperatureThe reaction mixture was cooled
  2. washwashed with saturated aqueous sodium bicarbonate solution, saturated ammonium chloride solution and brine
  3. dry with materialThe organics were dried (MgSO4)
  4. filtrationfiltered
  5. customsolvent removed in vacuo
  6. customto give a brown oil
  7. customThe oil was purified by silica chromatography (eluting with 0-100% ethyl acetate in petrol)

출처 및 근거

ORD 기록
ord-79d2a819b452424ea811f23102e76484
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09290456B2

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