N-methyl-2-pyrrolidone → HCID 68579778, 화합물

HRID 2233900노트

반응식

HRID 2233900 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].O1C=[CH:29][CH:28]=[C:27]1P(C1OC=CC=1)C1OC=CC=1.CN1C(=O)CCC1.C([Sn](CCCC)(CCCC)CCCC)C=C>CCOC(C)=O>[CH2:29]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH:28]=[CH2:27]

참가 물질

6

반응물 4

HCID 13387N-methyl-2-pyrrolidoneHCID 90628AllyltributylstannaneHCID 521585Tris(furan-2-yl)phosphaneHCID 68580010HCID 68580010, 화합물2회

생성물 1

HCID 68579778HCID 68579778, 화합물수율 774.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

Methyl 3-bromo-5-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}benzoate (Intermediate 104, 300 mg, 0.73 mmol), tris(dibenzylidineacetone)dipalladium (0) (26 mg, 0.03 mmol), trifurylphosphine (14 mg, 0.06 mmol) were weighed into a flask and placed under argon. NMP (3 ml) was added, followed by the dropwise addition of allyltributyl tin (0.25 ml, 0.80 mmol). The mixture was stirred at 100° C. After 64 h, the mixture was diluted with EtOAc and washed sequentially with water followed by brine. The organic phase was dried over MgSO4 and concentrated to dryness. The crude material was purified by chromatography on silica gel using 25% EtOAc/hexanes to give 174 mg of the title product.

후처리

  1. washwashed sequentially with water
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated to dryness
  4. customThe crude material was purified by chromatography on silica gel using 25% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-2d7099f7c9bf4f63bdc8f16684fcfa92
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709503B2

반응 노트

불러오는 중…