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Triethylamine → 4-(3-bromo-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamide

HRID 1666462
ノート
印刷プレビュー

反応式

HRID 1666462 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([CH:19]=[C:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][C:33](=O)[O:34]C2C=CC=CC=2)[CH:27]=1.C(N(CC)CC)C>CS(C)=O.O>[Br:1][C:2]1[CH:18]=[C:17]([CH:16]=[C:4]([O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=2)[CH:3]=1)[CH:19]=[C:20]1[CH2:25][CH2:24][N:23]([C:33]([NH:32][C:28]2[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=2)=[O:34])[CH2:22][CH2:21]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 668769892-(3-Bromo-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine

生成物 1

HCID 249679954-(3-bromo-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamide収率 67%

試薬・触媒・溶媒 2

HCID 679
Dimethyl Sulfoxide
溶媒
HCID 962Water溶媒

実験手順

2-(3-Bromo-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (0.58 g, 1.4 mmol) and phenyl pyridin-3-ylcarbamate (0.3 g, 1.4 mmol) were dissolved in DMSO (3 mL). Triethylamine (0.59 mL, 4.21 mmol) was added and the reaction was stirred overnight. The reaction mixture was diluted with water and extracted with ethyl acetate three times. The organic layer was washed with brine, dried over Na2SO4, and evaporated to dryness. The residue was purified by silica gel column chromatography (35% acetone in hexane) to give the title compound (0.5 g, 67%). 1H NMR (500 MHz, DMSO-d6): δ 8.44 (s, 2H), 8.25 (d, J=4.4 Hz, 1H), 7.99 (d, J=7.8 Hz, 1H), 7.92 (d, J=10.45 Hz, 1H), 7.22 (m, 2H), 7.20 (s, 1H), 7.04 (d, J=8.6 Hz, 1H), 6.93 (s, 1H), 6.83 (s, 1H), 6.34 (s, 1H), 3.60 (m, 2H), 3.52 (m, 2H), 2.56 (m, 2H), 2.44 (m, 2H). 13C NMR (125 MHz, CDCl3): δ 165.16, 154.72, 153.51, 145.38, 143.81, 141.22, 140.33, 139.66, 136.99, 136.36, 128.85, 127.64, 123.63, 123.26, 122.83, 122.48, 120.73, 111.68, 45.59, 44.60, 35.71, 29.29, 29.17; m/z (533.2, 535.2, M+ H+); HPLC: 99.0%.

後処理

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel column chromatography (35% acetone in hexane)

出典と根拠

ORDレコード
ord-547a9507579a42c2b5bde770ec4fc592
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08044052B2

反応ノート

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