Potassium Carbonate → Tert-butyl 1-bromo-7-cyano-2-naphthylcarbamate

HRID 2238423

반응식

HRID 2238423 반응식
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:10]2)=[CH:5][CH:4]=1)#[N:2].C1C(=O)N([Br:28])C(=O)C1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:28][C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[CH:12]=2)[CH:7]=[CH:8][C:9]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 44549667Tert-butyl 7-cyano-2-naphthylcarbamate

생성물 1

HCID 44549922Tert-butyl 1-bromo-7-cyano-2-naphthylcarbamate수율 100%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

A mixture of 193 (1.90 g, 7.09 mmol), NBS (1.41 g, 7.20 mmol) and K2CO3 (1.11 g, 8.50 mmol) in MeCN (20 mL) was heated at 60° C. under N2 for 30 min. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 and water. The organic layer was washed with water (×2), brine and dried. Filtration through silica gel gave tert-butyl 1-bromo-7-cyano-2-naphthylcarbamate (194) (2.45 g, 100%) as a colorless powder. A sample was recrystallised (petroleum ether) to give colorless needles: mp 139-141° C.; 1H NMR (CDCl3) δ 8.58 (d, J=9.1 Hz, 1H), 8.54 (d, J=1.0 Hz, 1H), 7.86 (d, J=8.4 Hz, 1H), 7.83 (d, J=9.1 Hz, 1H), 7.56 (dd; J=8.3, 1.4 Hz, 1H), 7.36 (br s, 1H), 1.57 (s, 9H); 13C NMR δ 152.3, 136.7, 132.5, 132.0, 131.4, 129.4, 128.3, 125.6, 122.4, 119.0, 111.3, 109.4, 81.9, 28.3. Anal. (C16H15BrN2O2) C, H, N, Br.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between CH2Cl2 and water
  3. washThe organic layer was washed with water (×2), brine
  4. customdried
  5. filtrationFiltration through silica gel

출처 및 근거

ORD 기록
ord-29b9b8c0bffb480e93949ea592bad6de
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718688B2

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