HCID 18468148, compound → HCID 18468208, compound

HRID 2229575Notes

Reaction equation

HRID 2229575 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8](=[O:24])[C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:12]([F:21])=[CH:11][C:10]=2[O:22]C)=[C:4]([F:27])[CH:3]=1.Br.CC(O)=O>>[Br:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8](=[O:24])[C:9]2[CH:14]=[C:13]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)[C:12]([F:21])=[CH:11][C:10]=2[OH:22])=[C:4]([F:27])[CH:3]=1

Participants

3

Reactant 2

HCID 18468148HCID 18468148, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 18468208HCID 18468208, compoundYield 88%

Procedure

A solution of N-(4-Bromo-2-fluoro-benzyl)-4-fluoro-2-methoxy-5-morpholin-4yl-benzamide (0.94 g, 24.1 mmol) in a 25% HBr/AcOH solution (25 mL) was heated to 100° C. for 6 h, cooled to room temperature and extracted with ethyl acetate. The crude product was filtered through a short pad of silica and concentrated to give the solid N-(4-bromo-2-fluoro-benzyl)-4-fluoro-2-hydroxy-5-morpholin-4-yl-benzamide (0.8 g, 88%): 1H NMR (DMSO-d6 300 MHz) δ 12.4 (s, 1H), 9.34 (br s, 1H), 8.12 (s, 1H), 8.05 (d, J=8.1 Hz, 1H), 7.72 (d, J=4.5 Hz, 1H), 7.56 (t, J=8.1 Hz, 1H), 7.47 (d, J=9.6 Hz, 1H), 6.69 (d, J=13.2 Hz, 1H), 4.56 (d, J=6 Hz, 2H), 3.65 (br d, J=3 Hz, 4H), 2.84 (br d, J=3 Hz, 4H).

Workup

  1. extractionextracted with ethyl acetate
  2. filtrationThe crude product was filtered through a short pad of silica
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2977f48348724e27acf37609e38289ca
Source dataset
uspto-grants-2002_07
Patent number
US06420426B1

Reaction notes

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