1,2-Dimethoxyethane → HCID 53861764、化合物

HRID 1507235ノート

反応式

HRID 1507235 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]=2)O1.C(COC)OC.[CH2:29]([O:36][C:37]1[CH:42]=[CH:41][C:40](Br)=[CH:39][CH:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:29]([O:36][C:37]1[CH:42]=[CH:41][C:40]([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:11][CH:10]=2)=[CH:39][CH:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

生成物 1

HCID 53861764HCID 53861764、化合物収率 82.6%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a stirring mixture of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (16.45 g, 53 mmol), dimethoxyethane (200 mL) and water (50 mL) was added 1-(benzyloxy)-4-bromobenzene (14 g, 53 mmol), sodium carbonate (16.9 g, 160 mmol) and bis-(triphenylphosphine)palladium(II) chloride (1.867 g, 2.66 mmol) at rt. The reaction mixture was purged with nitrogen for 15 min, then heated at 80° C. for 4 h. The mixture was allowed to cool to rt and then was filtered through Celite and diluted with 200 mL of water. The mixture was then extracted three times with 200 mL of ethyl acetate and the combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The residue was subjected to silica gel chromatography eluting with 20% ethyl acetate/petroleum ether to obtain 16 g of tert-butyl 4-(4-(benzyloxy)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (16 g, 82% yield) as an off-white solid. LCMS (method O) RT 1.32 min, m/z 366 (M+H+); 1H NMR (300 MHz, DMSO-d6) δ 1.47 (s, 9H), 2.42 (d, J=1.50 Hz, 2H), 3.52 (t, J=11.40 Hz, 2H), 3.97 (s, 2H), 5.11 (s, 2H), 6.04 (s, 1H), 6.98 (d, J=9.00 Hz, 2H), 7.30-7.46 (m, 7H).

後処理

  1. customThe reaction mixture was purged with nitrogen for 15 min
  2. temperatureto cool to rt
  3. filtrationwas filtered through Celite
  4. additiondiluted with 200 mL of water
  5. extractionThe mixture was then extracted three times with 200 mL of ethyl acetate
  6. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washeluting with 20% ethyl acetate/petroleum ether

出典と根拠

ORDレコード
ord-63a5221d8e5d467497bc91218d15cc48
出典データセット
uspto-grants-2015_12
特許番号
US09221796B2

反応ノート

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