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

HRID 390135Notes

Reaction equation

HRID 390135 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5e00149639494db9b242e374be8f9dd6
Source dataset
uspto-grants-2013_02
Patent number
US08383629B2

Reaction notes

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