Dichloromethane → HCID 57941180, compound

HRID 1437452Notes

Reaction equation

HRID 1437452 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:10][CH2:11][NH:12][CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH:14]=1.ClCCl.[C:26](OC(=O)C)(=[O:28])[CH3:27]>O>[C:26]([N:12]1[CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH:14]=[C:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[CH2:10][CH2:11]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 57941176HCID 57941176, compound

Product 1

HCID 57941180HCID 57941180, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stir bar equipped flask containing 4-(2,5-difluorophenyl)-6-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridne (1-5, 0.6 g, 0.19 mmol) was added dichloromethane (15 mL) followed successively by TEA (0.14 mL, 0.19 mmol), and acetic anhydride (0.06 mL, 0.59 mmol). The resulting solution stirred for 10 min. Water was added (2 mL), and then the reaction was washed with dichloromethane (2×30 mL). The organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude reside was purified by reverse phase liquid chromatography (0.1% TFA) to give 1-acetyl-4-(2,5-difluorophenyl)-6-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (1-6). 1H NMR (300 MHz, CDCl3) δ 7.26 (m, 1H), 6.96 (m, 4H), 6.82 (m, 1H); 6.36 (m, 1H), 6.20 (m, 1H), 3.82 (s, 3H), 3.80 (m, 2H); 3.40 (dt, J=11.9, 4.2 Hz, 1H); 2.74 (m, 1H); 2.42 (dd, J=16.0, 1.0 Hz, 1H), 2.20 (s, 3H); MS 344.1 found, 343.3 (M+H+) required.

Workup

  1. customTo a stir bar equipped flask
  2. washthe reaction was washed with dichloromethane (2×30 mL)
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude reside was purified by reverse phase liquid chromatography (0.1% TFA)

Sources & evidence

ORD record
ord-5762a4490344461ca20e96ce0cb582ed
Source dataset
uspto-grants-2009_11
Patent number
US07622489B2

Reaction notes

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