Triethylamine → HCID 10168896、化合物

HRID 352990ノート

反応式

HRID 352990 の反応式
[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]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 22706711HCID 22706711、化合物HCID 86594466HCID 86594466、化合物

生成物 1

HCID 10168896HCID 10168896、化合物収率 83.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-8fc7d8718346437bb4a5ce56c6cb3a8f
出典データセット
uspto-grants-2004_06
特許番号
US06749756B1

反応ノート

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