Boron tribromide → HCID 67419355, compound

HRID 571084Notes

Reaction equation

HRID 571084 reaction equation
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:12]=[C:11]([O:13]C)[C:10](=[O:15])[CH:9]=[C:8]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:12]=[C:11]([OH:13])[C:10](=[O:15])[CH:9]=[C:8]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67405781HCID 67405781, compound

Product 1

HCID 67419355HCID 67419355, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(Biphenyl-3-yl)-5-methoxy-2-phenylpyridin-4(1H)-one (20 mg, 0.056 mmol) was treated with BBr3 (0.5 mL of a 1 M solution in CH2Cl2) and stirred at room temperature. After 1 h, the reaction mixture was cooled to 0° C. and quenched with dropwise addition of MeOH (0.1 mL), before being concentrated under a stream of N2, diluted with MeOH (0.8 mL) and purified by reversed phase HPLC (2 cm×5 cm C18, acetonitrile-water gradient, 0.05% TFA added) to provide (99%) of 1-(biphenyl-3-yl)-5-hydroxy-2-phenylpyridin-4(1H)-one. 1H NMR (499 MHz, DMSO): δ 7.88 (s, 1 H); 7.64-7.60 (m, 2 H); 7.53 (d, J=7.7 Hz, 2 H); 7.46-7.40 (m, 3 H); 7.40-7.36 (m, 1 H); 7.30-7.26 (m, 6 H); 6.58 (s, 1 H). HRMS (ES) Calc (M+H)+ 340.1332 found 340.

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. customquenched with dropwise addition of MeOH (0.1 mL)
  3. concentrationbefore being concentrated under a stream of N2
  4. additiondiluted with MeOH (0.8 mL)
  5. custompurified by reversed phase HPLC (2 cm×5 cm C18, acetonitrile-water gradient, 0.05% TFA added)

Sources & evidence

ORD record
ord-65164803c4dc42a7b2cd73f4fdfe845d
Source dataset
uspto-grants-2015_05
Patent number
US09024032B2

Reaction notes

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