Boron tribromide → HCID 53379902, compound

HRID 625956Notes

Reaction equation

HRID 625956 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:12]([C:13]#[N:14])=[CH:11][C:10]([O:15]C)=[C:9]([O:17]C)[N:8]=2)[CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[C:1]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:8][C:9](=[O:17])[C:10]([OH:15])=[CH:11][C:12]=2[C:13]#[N:14])[CH:2]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67406460HCID 67406460, compound

Product 1

HCID 53379902HCID 53379902, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 2-(biphenyl-3-yl)-5,6-dimethoxypyridine-3-carbonitrile (17 mg, 0.054 mmol) in CH2Cl2 (1 mL) was added BBr3 solution (1 M in CH2Cl2, 0.537 mL) and stirred at 45° C. for 19 h. The reaction mixture was concentrated and the residue was stirred in 3 N aqueous HCl for 30 min. The precipitated white solid was collected by filtration and purified by preparative HPLC (5-50% CH3CN/H2O over 20 min, 0.05% added TFA) to give 2 mg (13%) of 2-(biphenyl-3-yl)-5-hydroxy-6-oxo-1,6-dihydropyridine-3-carbonitrile as a white solid. 1H NMR (500 MHz, CD3OD): δ 7.89 (s, 1H), 7.81 (d, J=7.2 Hz, 1H), 7.70 (d, J=7.6 Hz, 2H), 7.65-7.58 (m, 2H), 7.47 (t, J=7.6 Hz, 2H), 7.38 (t, J=7.4 Hz, 1H) 1 6.96 (s, 1H). High resolution mass spec (FT/ICR) calc (M+H)+=289.0972 found 289.0969.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. stirringthe residue was stirred in 3 N aqueous HCl for 30 min
  3. filtrationThe precipitated white solid was collected by filtration
  4. custompurified by preparative HPLC (5-50% CH3CN/H2O over 20 min, 0.05% added TFA)

Sources & evidence

ORD record
ord-e6b8ca195c7b48fd9205ca8cc3ad11e3
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

Loading…