Boron tribromide → HCID 53379904, compound

HRID 625962Notes

Reaction equation

HRID 625962 reaction equation
[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:8]([F:17])=[C:9]([O:15]C)[C:10]([O:13]C)=[N:11][CH:12]=2)[CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:8]([F:17])=[C:9]([OH:15])[C:10](=[O:13])[NH:11][CH:12]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67406064HCID 67406064, compound

Product 1

HCID 53379904HCID 53379904, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(biphenyl-3-yl)-4-fluoro-2,3-dimethoxypyridine (15 mg, 0.048 mmol) in CH2Cl2 (1 mL) was added a methylene chloride solution of BBr3 (1 M, 0.97 mL). After 24 h of stirring at room temperature, the reaction mixture was concentrated and the resulting residue was stirred in 3 N aqueous HCl as a suspension for 1 h. Concentrated, triturated with MeOH and the precipitated solid was collected by filtration, washed with MeOH and dried in vacuo to afford 12 mg (88%) of 5-biphenyl-3-yl-4-fluoro-3-hydroxypyridin-2(1H)-one as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 12.12 (s, 1H), 9.45 (s, 1H), 7.77-7.69 (m, 3H), 7.66-7.64 (m, 1H), 7.54-7.37 (m, 5H), 7.23 (d, J=8.8 Hz, 1H). High resolution mass spec (FT/ICR) calc (M+H)+=282.0925 found 282.0921.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. stirringthe resulting residue was stirred in 3 N aqueous HCl as a suspension for 1 h
  3. concentrationConcentrated
  4. customtriturated with MeOH
  5. filtrationthe precipitated solid was collected by filtration
  6. washwashed with MeOH
  7. customdried in vacuo

Sources & evidence

ORD record
ord-f03a488a148c47baade10df4c82dfafb
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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