Phenylboronic Acid → HCID 69171162, 화합물

HRID 2374449

반응식

HRID 2374449 반응식
[C:1]([O:5][C:6](=[O:32])[CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24](Cl)=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=3)[CH:15]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2C2C=CC=CC=2)C2CCCCC2)CCCCC1.[F-].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1COCC1>[C:1]([O:5][C:6](=[O:32])[CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=3)[CH:15]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 691740893-[6-(4-chloro-3-trifluoromethyl-phenoxymethyl)-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid tert-butyl ester

생성물 1

HCID 69171162HCID 69171162, 화합물

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
120 °C

실험 절차

A microwave vial is charged with 3-[6-(4-chloro-3-trifluoromethyl-phenoxymethyl)-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid tert-butyl ester (56 mg, 0.119 mmol), phenylboronic acid (17 mg, 1.2 eq.), Pd(OAc)2 (1.3 mg, 5 mol %), (dicyclohexylphosphino)biphenyl (4.2 mg, 10 mol %), KF (21 mg, 3 eq.), and THF (0.25 mL). The resulting mixture is heated to 120° C. using microwave irradiation for 20 minutes. The mixture is filtered through celite. The celite is washed with EtOAc several times. The filtrate is then concentrated to give a dark oil. The mixture is purified by column chromatography (silica gel, EtOAc/Hexane, gradient) to give 3-[6-(2-trifluoromethyl-biphenyl-4-yloxymethyl)-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid tert-butyl ester.

후처리

  1. custommicrowave irradiation for 20 minutes
  2. filtrationThe mixture is filtered through celite
  3. washThe celite is washed with EtOAc several times
  4. concentrationThe filtrate is then concentrated
  5. customto give a dark oil
  6. customThe mixture is purified by column chromatography (silica gel, EtOAc/Hexane, gradient)

출처 및 근거

ORD 기록
ord-c6932c5e352b4a79b4e1aefcbc705ecf
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462629B2

연결된 노트

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