Phenylboronic Acid → HCID 69171162、化合物

HRID 2374449

反応式

HRID 2374449 の反応式
[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]

参加物

7

反応物 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

生成物 1

HCID 69171162HCID 69171162、化合物

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c6932c5e352b4a79b4e1aefcbc705ecf
出典データセット
uspto-grants-2008_12
特許番号
US07462629B2

関連ノート

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