Phthalimide → trans-2-{[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}-1H-isoindole-1,3(2H)-dione

HRID 1639784ノート

反応式

HRID 1639784 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[C@@H:12]1[CH2:14][C@H:13]1[CH2:15]O.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:48]1(=[O:58])[NH:52][C:51](=[O:53])[C:50]2=[CH:54][CH:55]=[CH:56][CH:57]=[C:49]12>O1CCCC1.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[C@@H:12]1[CH2:14][C@H:13]1[CH2:15][N:52]1[C:48](=[O:58])[C:49]2[C:50](=[CH:54][CH:55]=[CH:56][CH:57]=2)[C:51]1=[O:53]

参加物

7

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66720702trans-[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methanol

生成物 1

HCID 66720673trans-2-{[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}-1H-isoindole-1,3(2H)-dione

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of trans-[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methanol (500 mg, 2.27 mmol) in tetrahydrofuran (22 mL) were added a solution (40%, 1.24 mL, 2.72 mmol) of diethyl azodicarboxylate in toluene, triphenylphosphine (774 mg, 2.95 mmol) and phthalimide (434 mg, 2.95 mmol), and the mixture was stirred under nitrogen atmosphere at room temperature for 1.5 hr. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=10/90→40/60) to give trans-2-{[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}-1H-isoindole-1,3(2H)-dione as a crudely purified product (893 mg).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=10/90→40/60)

出典と根拠

ORDレコード
ord-cc8cd5f401554c40880bd8ff20b6448b
出典データセット
uspto-grants-2012_02
特許番号
US08110585B2

反応ノート

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