Pyridine → HCID 67515825, compound

HRID 1754335Notes

Reaction equation

HRID 1754335 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[CH:5]=[N:6][OH:7].N1C=CC=CC=1.ClN1C(=O)CCC1=O.[CH2:26]=[C:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.C(N(CC)CC)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[CH2:26][C:27]3([CH2:31][CH2:30][CH2:29][CH2:28]3)[O:7][N:6]=2)[CH:8]=[CH:9][C:10]=1[CH3:11]

Participants

7

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 73714Cyclopentane, methylene-HCID 86694674HCID 86694674, compound

Product 1

HCID 67515825HCID 67515825, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-bromo-4-methylbenzaldehyde oxime (0.85 g, 4 mmol, 1.0 eq) in THF (50 mL) was added pyridine (0.2 mL, 2.4 mmol, 0.6 eq) followed by N-chlorosuccinimide (530 mg, 4 mmol, 1.0 eq) and the resulting mixture was refluxed for 1 h. The reaction was cooled to room temperature before the addition of a solution of methylenecyclopentane (0.42 mL, 4 mmol, 1.0 eq) in THF (5 mL) followed by triethyl amine (0.94 mL, 7 mmol, 1.7 eq). The resulting solution was refluxed for 1 h. The solvent was evaporated under vacuum and usual work up afforded 690 mg of the title product as a white solid. 1HNMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.24 (d, J=8.0 Hz, 1H), 3.22 (s, 2H), 2.41 (s, 3H), 2.14-2.11 (m, 2H), 1.88-1.84 (m, 2H), 1.77-1.72 (m, 4H); ESI-MS (m/z) 294, 296 [(MH)+, Br79,81].

Workup

  1. temperaturethe resulting mixture was refluxed for 1 h
  2. temperatureThe resulting solution was refluxed for 1 h
  3. customThe solvent was evaporated under vacuum and usual work

Sources & evidence

ORD record
ord-5f52ff38abac47c3b0e7b2f25d72ee42
Source dataset
uspto-grants-2015_10
Patent number
US09169242B2

Reaction notes

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