Benzene, 1-bromo-4-(trifluoromethyl)- → HCID 25065679, 화합물

HRID 42201

반응식

HRID 42201 반응식
[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=1.CC(C)([O-])C.[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 64040231-Benzyl-4-piperazin-1-yl-phthalazineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23665647Potassium tert-butoxide

생성물 1

HCID 25065679HCID 25065679, 화합물수율 37%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
110 °C

실험 절차

To a solution of 1-benzyl-4-piperazin-1yl-phthalazine (100 mg, 0.329 mmol) in 1 mL THF is added 4-bromo-benzotrifluoride (99 mg, 0.443 mmol), potassium tert-butoxide (55.3 mg, 0.493 mmol), XPhos [2-(Dicyclohexylphosphino)-2′,4′,6′-tri-1-propyl-1′-1′-biphenyl] (15.7 mg, 0.033 mmol), and palladium (II) acetate (11 mg, 0.16 mmol) in a 2 dram screw-top vial. The vial is evacuated and flushed with argon. The reaction mixture was heated to 110° C. for 18 hrs. The mixture is then poured into water (50 mL), and the precipitate is isolated by filtration. The resulting solid is purified by flash chromatography on silica gel (10-70% EtOAc:heptanes) to provide the desired product as yellow crystals (54 mg, 37% yield).

후처리

  1. customThe vial is evacuated
  2. customflushed with argon
  3. additionThe mixture is then poured into water (50 mL)
  4. customthe precipitate is isolated by filtration
  5. customThe resulting solid is purified by flash chromatography on silica gel (10-70% EtOAc:heptanes)

출처 및 근거

ORD 기록
ord-a0263b0c12aa448d90f3cddfd3abef19
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536168B2

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