Methanol → HCID 117771602, compound

HRID 2201521Notes

Reaction equation

HRID 2201521 reaction equation
C([O:8][C:9]1[C:10]([C:16]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[O:17])=[N:11][C:12]([Br:15])=[CH:13][CH:14]=1)C1C=CC=CC=1.B(Br)(Br)Br.CO.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Br:15][C:12]1[N:11]=[C:10]([C:16]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[O:17])[C:9]([OH:8])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 117771250HCID 117771250, compound

Product 1

HCID 117771602HCID 117771602, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(benzyloxy)-6-bromo-N-(4-fluorobenzyl)picolinamide (50 mg, 0.11 mmol) in CH2Cl2 (5 mL) was added BBr3 (1.5 mL) dropwise at −78° C. under N2. The mixture was allowed to room temperature and stirred for another 12 hours. Then CH3OH was added and the mixture was adjusted to pH=7 by saturated K2CO3. The mixture was extracted with EtOAc and the combined organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by prep-TLC (PE:EtOAc=5:1) to afford the product of 6-bromo-N-(4-fluorobenzyl)-3-hydroxypicolinamide (20 mg, yield: 57%). 1H-NMR (CDCl3, 400 MHz) δ 12.04 (s, 1H), 8.02 (s, 1H), 7.39 (d, J=8.8 Hz, 1H), 7.24˜7.28 (m, 2H), 7.15 (d, J=8.8 Hz, 1H), 6.96˜7.00 (m, 2H), 4.52 (d, J=6.4 Hz, 2H). MS (M+H)+: 325/327.

Workup

  1. customwas allowed to room temperature
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by prep-TLC (PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-3dd950f27ed447968aea055bb69e3362
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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