Pyridine → HCID 59799037, compound

HRID 1013108Notes

Reaction equation

HRID 1013108 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(C)C1C=CN=CC=1>[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, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Under a 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), 4-(dimethylamino)pyridine (222 mg, 1.8 mmol) and acetic anhydride (30 mL). Heat the mixture at reflux for 8 h and stir at RT for another 8 h Concentrate, dilute the residue in EtOAc, wash with 1 N HCl, and then with saturated aqueous sodium bicarbonate solution. Dry (sodium sulfate) and concentrate to give the title compound that was used in the next step without further purification.

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux for 8 h
  3. concentrationConcentrate
  4. additiondilute the residue in EtOAc
  5. washwash with 1 N HCl
  6. dry with materialDry (sodium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-5db9ab45e79c4f3fb7431ecc69a27d13
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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