Triethylamine → HCID 10168896, 화합물

HRID 352990노트

반응식

HRID 352990 반응식
[OH:1][CH:2]([C:5]1[CH:10]=[C:9]([I:11])[N:8]([CH2:12][C:13]#[CH:14])[C:7](=[O:15])[C:6]=1[CH3:16])[CH2:3][CH3:4].CCN(CC)CC.Br[Si:25]([CH:44]([CH3:46])[CH3:45])([CH:41]([CH3:43])[CH3:42])[CH2:26][CH2:27][C:28]([F:40])([F:39])[C:29]([F:38])([F:37])[C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:44]([Si:25]([CH:41]([CH3:43])[CH3:42])([CH2:26][CH2:27][C:28]([F:40])([F:39])[C:29]([F:37])([F:38])[C:30]([F:35])([F:36])[C:31]([F:32])([F:33])[F:34])[O:1][CH:2]([C:5]1[CH:10]=[C:9]([I:11])[N:8]([CH2:12][C:13]#[CH:14])[C:7](=[O:15])[C:6]=1[CH3:16])[CH2:3][CH3:4])([CH3:45])[CH3:46]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 22706711HCID 22706711, 화합물HCID 86594466HCID 86594466, 화합물

생성물 1

HCID 10168896HCID 10168896, 화합물수율 83.4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-(1-hydroxypropyl)-6-iodo-3-methyl-1-prop-2-ynyl-1H-pyridin-2-one 4b (44 mg, 0.13 mmol) and 4-dimethylaminopyridine (2 mg, 1.2 μmol) in CH2Cl2 (2 mL) was added NEt3 (53 mg, 74 μL, 0.52 mmol) and bromodiisopropyl(3, 3, 4, 4, 5, 5, 6, 6, 6-nonafluorohexyl)silane (147 mg, 0.33 mmol, prepared by mixing diisopropyl-(3, 3, 4, 4, 5, 5, 6, 6, 6-nonafluorohexyl)silane and Br2) and the mixture was stirred for 12 h. The solvent was evaporated and the residue was purified by flash chromatography (hexanes-EtOAc 15:1) to afford 5b (75 mg, 82%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ6.99 (s, 1H), 5.12 (d, J=16.5, 1H), 5.00 (d, J=16.5, 1H), 4.75 (t, J=6.0 Hz, 1H), 2.33-2.31 (m, 1H), 2.07-1.99 (m, 2H) 2.06 (s, 3H), 1.84-1.60 (m, 2H), 1.00 (s, 14H), 0.88 (t, J=7.4 Hz, 3H), 0.83-0.79 (m, 2H); 13C NMR (75 MHz, CDCl3) δ162.4, 152.5, 123.7, 118.6, 94.2, 72.8, 71.5, 44.3, 31.1, 25.3, 17.5, 12.6, 9.4, 0.3.

후처리

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography (hexanes-EtOAc 15:1)

출처 및 근거

ORD 기록
ord-8fc7d8718346437bb4a5ce56c6cb3a8f
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06749756B1

반응 노트

불러오는 중…