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

HRID 390135노트

반응식

HRID 390135 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5e00149639494db9b242e374be8f9dd6
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383629B2

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