Sodium hydride → Tert-butyl 1-bromo-7-cyano-2-naphthyl(3-chloro-2-propen-1-yl)carbamate

HRID 2238424

반응식

HRID 2238424 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].[H-].[Na+].[Cl:24][CH:25]=[CH:26][CH2:27]Cl>CN(C=O)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[N:14]([CH2:27][CH:26]=[CH:25][Cl:24])[C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 248831,3-DichloropropeneHCID 44549922Tert-butyl 1-bromo-7-cyano-2-naphthylcarbamate

생성물 1

HCID 75066243Tert-butyl 1-bromo-7-cyano-2-naphthyl(3-chloro-2-propen-1-yl)carbamate수율 107.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 194 (2.50 g, 7.21 mmol) in DMF (20 mL) was added to a suspension of NaH (350 mg, 8.65 mmol, 60% in oil) in DMF (20 mL) at 0° C. 1,3-Dichloropropene (1.60 g, 14 mmol) was added and the mixture was allowed to warm to room temperature over 2 h. The DMF was removed under reduced pressure and the residue was partitioned between CH2Cl2 and water. The organic layer was washed with water (×2), brine (×2) and dried. Filtration through silica gel gave tert-butyl 1-bromo-7-cyano-2-naphthyl(3-chloro-2-propen-1-yl)carbamate (195) (3.28 g, 100%) as a pale yellow oil; 1H NMR (CDCl3) (mixture of rotamers and E and Z forms) δ 8.73 (s, 1H), 7.93-7.96 (m, 1H), 7.83-7.87 (m, 1H, 7.68-7.70 (m, 1H), 7.39-7.46 (m, 1H), 6.00-6.11 (m, 2 H), 4.49-4.62 (m, 1H), 4.33-4.43 (m, 1H), 1.33, 1.32 (2's, 9 W. HRMS (FAB) calcd. for C19H1879Br35ClN2O2 (MH+) m/z 421.0318, found 421.0330.

후처리

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

출처 및 근거

ORD 기록
ord-7e3ae6cd7df0460ea8e9410fc5c8daec
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718688B2

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