Pyridine → HCID 59799037, compound

HRID 2041124Notes

Reaction equation

HRID 2041124 reaction equation
[Br:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:11][CH2:12][C:6]=2[C:5]([OH:19])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>CN(C1C=CN=CC=1)C>[C:26]([O:19][C:5]1[C:6]2[CH2:12][CH2:11][N:10]([C:13](=[O:18])[C:14]([F:16])([F:17])[F:15])[CH2:9][CH2:8][C:7]=2[C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 59799046HCID 59799046, compound

Product 1

HCID 59799037HCID 59799037, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Under nitrogen atmosphere, mix 9-bromo-6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (6 g, 17.8 mmol), anhydrous pyridine (0.06 mL, 0.72 mmol), DMAP (222 mg, 1.8 mmol) and acetic anhydride (30 mL). Heat the mixture at reflux for 8 h and then stir at ambient temperature for another 8 h. Concentrate in vacuo, dilute the residue in EtOAc, wash with 1N aqueous HCl, and then with saturated aqueous NaHCO3. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain the desired intermediate (5.64 g, 84%) that was used without further purification. MS (ES+) m/z: 380 (M+H)+.

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux for 8 h
  3. concentrationConcentrate in vacuo
  4. additiondilute the residue in EtOAc
  5. washwash with 1N aqueous HCl
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-9dce60e8fbcb4278a0217ca49a0287d3
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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