Sodium hydride → HCID 75066177, 화합물

HRID 2238394

반응식

HRID 2238394 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][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.O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][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

6

반응물 3

HCID 24758Sodium hydrideHCID 248831,3-DichloropropeneHCID 44549797Tert-butyl 1-bromo-6-cyano-2-naphthylcarbamate

생성물 1

HCID 75066177HCID 75066177, 화합물수율 96.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A stirred solution of nitrile 141 (5.78 g, 16.6 mmol) in dry DMF (50 mL) was treated at 0° C. with NaH (0.80 g, 20.0 mmol, 60% in oil). The resulting suspension was warmed to room temperature for 30 min, then cooled to 0° C. again and treated with 1,3-dichloropropene (4.8 mL, 52 mmol, mixed isomers). After stirring at room temperature for a further 6 h, the mixture was diluted with water and extracted with EtOAc (×3). The combined organic extracts were washed with water (×3), dried, and concentrated to dryness under high vacuum at 80° C. The residue was chromatographed on silica gel, eluting with CH2Cl2, to give tert-butyl 1-bromo-6-cyano-2-naphthyl(3-chloro-2-propenyl)carbamate (142) (6.77 g, 96%) as a foam; 1H NMR [(CD3)2SO] (mixture of rotamers and E and Z forms) δ 8.69 (s, 1H), 8.35 (d, J=8.8 Hz, 1H), 8.13, 8.12 (2 d, J=8.6 Hz, 1H), 7.96 (d, J=8.9 Hz, 1H), 7.69, 7.63 (2d, J=8.7 Hz, 1H), 6.42-6.29 (m, 1H), 6.17-5.99 (m, 1H), 4.55-4.45, 4.40-4.19, 4.15-3.98 (3 m, 2H), 1.48, 1.24 (2 s, 9H). HRMS (FAB) calcd. for C19H1979Br35ClN2O2(m/z 421.0318, found 421.0306.

후처리

  1. temperaturecooled to 0° C. again
  2. extractionextracted with EtOAc (×3)
  3. washThe combined organic extracts were washed with water (×3)
  4. customdried
  5. concentrationconcentrated to dryness under high vacuum at 80° C
  6. customThe residue was chromatographed on silica gel
  7. washeluting with CH2Cl2

출처 및 근거

ORD 기록
ord-e07fb6c1a29a4c88b0327648948e626c
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718688B2

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