2,2,2-Trifluoro-1-(6-fluoro-1,2,4,5-tetrahydro-9-methoxy-3H-3-benzazepin-3-yl)ethanone → HCID 89648453, compound

HRID 1774000Notes

Reaction equation

HRID 1774000 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH2:10][C:9]2[C:12]([F:18])=[CH:13][CH:14]=[C:15]([O:16]C)[C:8]=2[CH2:7][CH2:6]1)=O>C(Cl)Cl.B(Br)(Br)Br>[F:18][C:12]1[C:9]2[CH2:10][CH2:11][NH:5][CH2:6][CH2:7][C:8]=2[C:15]([OH:16])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 576562002,2,2-Trifluoro-1-(6-fluoro-1,2,4,5-tetrahydro-9-methoxy-3H-3-benzazepin-3-yl)ethanone

Product 1

HCID 89648453HCID 89648453, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

To a solution of 2,2,2-trifluoro-1-(6-fluoro-9-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone (1.22 g, 4.19 mmol, 1 eq.) in DCM (50 mL), 1M boron tribromide solution in dichloromethane (8.38 mL) was added. The mixture was stirred at r.t. for 2 hours. The reaction was carefully quenched with 2N aq. NaOH soln. (50 mL) and stirred at r.t. for 30 min. The reaction mixture was washed with DCM (2×50 mL). The aq. layer was concentrated in vacuo. The residue was purified by prep. HPLC (column: Water X-Bridge, 30×75 mm, 10 um, UV/MS, basic conditions) and concentrated in vacuo to give the desired product.

Workup

  1. customThe reaction was carefully quenched with 2N aq. NaOH soln
  2. stirring(50 mL) and stirred at r.t. for 30 min
  3. washThe reaction mixture was washed with DCM (2×50 mL)
  4. concentrationThe aq. layer was concentrated in vacuo
  5. customThe residue was purified by prep
  6. concentrationHPLC (column: Water X-Bridge, 30×75 mm, 10 um, UV/MS, basic conditions) and concentrated in vacuo

Sources & evidence

ORD record
ord-1daa3c3a0305417099dad0a5974eda85
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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