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

HRID 1392232
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HRID 1392232 반응식
[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]
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참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 962Water용매
HCID 6228Dimethylformamide용매

실험 절차

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%)

후처리

  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)

출처 및 근거

ORD 기록
ord-01ef786061ec438693154980bc49804b
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07342030B2

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