Pyridine → HCID 59799037, compound

HRID 911235Notes

Reaction equation

HRID 911235 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-79f2841632524c60a5016d383f56a12b
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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