Pyridine → HCID 86667165, compound

HRID 2367937Notes

Reaction equation

HRID 2367937 reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][CH2:7][C@@H:6]([O:10][C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:5]1[OH:30])=[N+:2]=[N-:3].N1C=CC=CC=1.[C:37](Cl)([CH3:39])=[O:38]>C(Cl)Cl>[C:37]([O:30][C@H:5]1[C@H:6]([O:10][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:7][CH2:8][CH2:9][C@@H:4]1[N:1]=[N+:2]=[N-:3])(=[O:38])[CH3:39]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86667162HCID 86667162, compound

Product 1

HCID 86667165HCID 86667165, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound 2 (625 mg, 1.57 mmol), pyridine (363 μL, 4.69 mmol) and AcCl (272 μL, 3.13 mmol) were dissolved in CH2Cl2 (15 mL) under nitrogen atmosphere at room temperature. After 2 h the mixture was diluted with CH2Cl2. The organic layer was washed (HCl(aq) 5%, sat NaHCO3, brine), dried (MgSO4), filtered and concentrated. No further purification was needed. The reaction yielded 100% of 3. 1H-NMR (CDCl3) 7.45 (m, 6 H), 7.20-7.35 (m, 9 H), 5.14 (t, J=9.49 Hz, 1 H), 2.99-3.10 (m, 2 H), 1.93 (s, 3 H), 1.86 (m, 1 H), 1.50 (m, 2 H), 1.25-1.40 (m, 2 H), 0.80 (m, 1 H).

Workup

  1. washThe organic layer was washed (HCl(aq) 5%, sat NaHCO3, brine)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customNo further purification

Sources & evidence

ORD record
ord-17229bbd59e24aeda2b168744b568fee
Source dataset
uspto-grants-2014_04
Patent number
US08703720B2

Reaction notes

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