Triethylamine → tert-butyl 4-(3-bromo-2-iodo-N-(4-methoxybenzyl)benzamido)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 390135ノート

反応式

HRID 390135 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1.[Br:25][C:26]1[C:27]([I:35])=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30].CCN(CC)CC>O.C1(C)C=CC=CC=1>[Br:25][C:26]1[C:27]([I:35])=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29]([N:22]([C:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH:10]=1)[CH2:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)=[O:30]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 582956743-Bromo-2-iodo-benzoyl chloride

生成物 1

HCID 58295704tert-butyl 4-(3-bromo-2-iodo-N-(4-methoxybenzyl)benzamido)-5,6-dihydropyridine-1(2H)-carboxylate収率 63%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
100 °C

実験手順

A mixture of tert-butyl-4-oxopiperidine-1-carboxylate (19 g, 0.0.096 mol), 4-methoxybenzylamine (13 g, 0.096 mol) and toluene was stirred at 100° C. for 3 h and then concentrated to give a residue. Toluene (300 mL), 3-bromo-2-iodo-benzoyl chloride (25 g, 0.077 mol), and Et3N (24.5 g, 0.23 mol) were added to the residue and the mixture was stirred at 80° C. overnight. The mixture was cooled, and poured into water and extracted with EtOAc. The organic layer was dried and concentrated to give the crude product which was purified by column chromatography to afford tert-butyl 4-(3-bromo-2-iodo-N-(4-methoxybenzyl)benzamido)-5,6-dihydropyridine-1(2H)-carboxylate (30 g, 63%). 1H NMR: (400 MHz, MeOD): δ=1.38 (s, 9H), 1.43 (m, 2H), 1.48 (m, 4H), 1.63 (m, 2H), 3.18 (m, 2H), 3.60 (m, 2H), 3.80 (s, 3H), 4.55 (d, 1H), 5.49 (m, 1H), 6.88 (m, 3H), 7.02 (m, 2H), 7.16 (m, 1H), 7.32 (m, 3H), 7.55 (m, 1H).

後処理

  1. concentrationconcentrated
  2. customto give a residue
  3. stirringthe mixture was stirred at 80° C. overnight
  4. temperatureThe mixture was cooled
  5. extractionextracted with EtOAc
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customto give the crude product which
  9. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-5e00149639494db9b242e374be8f9dd6
出典データセット
uspto-grants-2013_02
特許番号
US08383629B2

反応ノート

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