Boron tribromide → HCID 53379903, compound

HRID 625959Notes

Reaction equation

HRID 625959 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:8]([C:17]#[N:18])=[N:9][C:10]([O:15]C)=[C:11]([O:13]C)[CH:12]=2)[CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[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[CH:12]=[C:11]([OH:13])[C:10](=[O:15])[NH:9][C:8]=2[C:17]#[N:18])[CH:2]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 674080083-[1,1′-Biphenyl]-3-yl-5,6-dimethoxy-2-pyridinecarbonitrile

Product 1

HCID 53379903HCID 53379903, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(biphenyl-3-yl)-5,6-dimethoxypyridine-2-carbonitrile (34 mg, 0.107 mmol) in CH2Cl2 (1 mL) was added BBr3 solution (1 M in CH2Cl2, 2.149 mL) and stirred at 50° C. for 21 h. The reaction mixture was concentrated and the residue was stirred in 3 N aqueous HCl. After 1 h, this mixture was concentrated and purified by preparative HPLC (5-60% CH3CN/H2O over 20 min, 0.05% added TFA) to give 17 mg (55%) of 3-(biphenyl-3-yl)-5-hydroxy-6-oxo-1,6-dihydropyridine-2-carbonitrile as a light pink solid. 1H NMR (400 MHz, CDCl3): δ 7.75-7.65 (m, 2H), 7.65-7.53 (m, 3H), 7.47 (t, J=8.0 Hz, 3H), 7.39 (t, J=7.6 Hz, 1H), 7.12 (s, 1H). LC/MS (M+H)+ 289.2.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. stirringthe residue was stirred in 3 N aqueous HCl
  3. waitAfter 1 h
  4. concentrationthis mixture was concentrated
  5. custompurified by preparative HPLC (5-60% CH3CN/H2O over 20 min, 0.05% added TFA)

Sources & evidence

ORD record
ord-8c62e8f033654f8ba8e28f9d412e244d
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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