Boron tribromide → HCID 178515098, compound

HRID 222319Notes

Reaction equation

HRID 222319 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[C:14]([F:20])=[C:15]([O:18]C)[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[C:14]([F:20])=[C:15]([OH:18])[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 577228443-chloro-6-fluoro-7-methoxy-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

Product 1

HCID 178515098HCID 178515098, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-chloro-6-fluoro-7-methoxy-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (2.0 g, 6.9 mmol) in CH2Cl2 (100 mL) was added BBr3 (1 M in CH2Cl2, 27.6 mL, 27.6 mmol) at −78° C. The mixture was allowed to warm to room temperature as the bath did. After 6 h at room temperature, the mixture was cooled to 0° C. and treated with aqueous NaHCO3 solution. The yellow precipitate was filtered, washed with CH2Cl2, and dried under high-vacuum overnight to afford the title compound. 1H NMR (600 MHz, CD3SOCD3) δ 8.93 (d, 1H); 8.28 (d, 1H); 7.46 (d, 1H); 7.37 (d, 1H); 7.33 (t, 1H); 7.08 (d, 1H). LRMS (ESI) calc'd for (C14H7ClFNO2) [M+H]+, 276.0; found 276.0.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. filtrationThe yellow precipitate was filtered
  3. washwashed with CH2Cl2
  4. customdried under high-vacuum overnight

Sources & evidence

ORD record
ord-b32ec742280d45288b2bfa6adaf9547f
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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