Triethylamine → HCID 66876192, compound

HRID 1666523Notes

Reaction equation

HRID 1666523 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH:5]=[C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.[CH3:22][O:23][C:24]1[N:29]=[C:28]([CH3:30])[C:27](B(O)O)=[CH:26][CH:25]=1.[CH2:34](N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:22][O:23][C:24]1[N:29]=[C:28]([CH3:30])[C:27]([CH2:34][C:2]2[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=2)[CH:5]=[C:6]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27630842-Methyl-6-methoxypyridine-3-boronic acidHCID 53485958Tert-butyl 4-(3-hydroxybenzylidene)piperidine-1-carboxylate

Product 1

HCID 66876192HCID 66876192, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-Butyl 4-(3-hydroxybenzylidene)piperidine-1-carboxylate (1 g, 3 mmol; Example 57, Step 3), 6-methoxy-2-methylpyridin-3-ylboronic acid (1.15 g, 6 mmol), copper acetate (0.627 g, 3 mmol), 4 Å molecular sieves, and triethylamine (2.40 mL, 15 mmol) in dichloromethane (5 mL) was stirred at r.t for 48 hours. The reaction mixture was filtered through a celite bed, and the filtrate was concentrated under reduced pressure and purified by column chromatography (3.5% ethyl acetate/hexane) to give the title compound (0.42 g, 30% yield). 1HNMR (500 MHz, CDCl3): δ ppm 7.20 (m, 2H), 6.86 (d, J=7.45 Hz, 1H), 6.68 (m, 2H), 6.59 (d, J=8.6 Hz, 1H), 6.28 (s, 1H), 3.94 (s, 1H), 3.49 (s, 2H), 3.38 (s, 2H), 2.42 (s, 2H), 2.36 (s, 3H), 2.31 (d, J=5.45 Hz, 2H), 1.47 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through a celite bed
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. custompurified by column chromatography (3.5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-695f8d7cb26d4055a980ee34b187a311
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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