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Tetrahydrofuran → [2-Fluoro-4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-carbamic acid tert-butyl ester

HRID 1392232
ノート
印刷プレビュー

反応式

HRID 1392232 の反応式
[CH2:1]([N:5]1[CH:9]=[CH:8][N:7]=[N:6]1)[CH2:2][CH:3]=[CH2:4].C1COCC1.[C:15]([O:19][C:20](=[O:30])[NH:21][C:22]1[CH:27]=[CH:26][C:25](Br)=[CH:24][C:23]=1[F:29])([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[C:15]([O:19][C:20](=[O:30])[NH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:4][CH2:3][CH2:2][CH2:1][N:5]2[CH:9]=[CH:8][N:7]=[N:6]2)=[CH:24][C:23]=1[F:29])([CH3:18])([CH3:16])[CH3:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 190682081-but-3-enyl-1H-[1,2,3]triazoleHCID 22736228tert-butyl N-(4-bromo-2-fluorophenyl)carbamate

生成物 1

HCID 69220904[2-Fluoro-4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-but-3-enyl-1H-[1,2,3]triazole (0.85 g, 6.9 mmol) in THF (15 ml) 9-borabicyclo[3.3.1]nonane (0.5 M in THF, 30.3 ml, 15.2 mmol) was added dropwise at 0° C. and stirring continued for 2 h. This mixture was then added to a solution of (4-bromo-2-fluoro-phenyl)-carbamic acid tert-butyl ester (2 g, 6.89 mmol), Pd(dppf)Cl2 (0.56 g, 0.69 mmol) and aqueous cesium carbonate (6.89 ml, 3M) in DMF (30 ml) and stirred for 3 h at 70° C. Water (100 ml) was added and the mixture extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated. The crude product was purified on silica gel (ethyl acetate) to yield [2-Fluoro-4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-carbamic acid tert-butyl ester as light yellow solid. Yield 1.93 g (84%)

後処理

  1. stirringstirred for 3 h at 70° C
  2. extractionthe mixture extracted with ethyl acetate (3×100 ml)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified on silica gel (ethyl acetate)

出典と根拠

ORDレコード
ord-01ef786061ec438693154980bc49804b
出典データセット
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07342030B2

反応ノート

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