Hydrogen Bromide → N-[3-tert-Butyl-2-methoxy-5-(2-oxo-1,2-dihydro-pyridin-3-yl)-phenyl]-2-fluoro-4-hydroxy-benzamide

HRID 2390876Notes

Reaction equation

HRID 2390876 reaction equation
C([O:8][C:9]1[CH:37]=[CH:36][C:12]([C:13]([NH:15][C:16]2[CH:21]=[C:20]([C:22]3[C:23]([O:28]C)=[N:24][CH:25]=[CH:26][CH:27]=3)[CH:19]=[C:18]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:17]=2[O:34][CH3:35])=[O:14])=[C:11]([F:38])[CH:10]=1)C1C=CC=CC=1.Br>CC(O)=O>[C:30]([C:18]1[C:17]([O:34][CH3:35])=[C:16]([NH:15][C:13](=[O:14])[C:12]2[CH:36]=[CH:37][C:9]([OH:8])=[CH:10][C:11]=2[F:38])[CH:21]=[C:20]([C:22]2[C:23](=[O:28])[NH:24][CH:25]=[CH:26][CH:27]=2)[CH:19]=1)([CH3:33])([CH3:31])[CH3:32]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 670699134-benzyloxy-N-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-2-fluoro-benzamide

Product 1

HCID 67070270N-[3-tert-Butyl-2-methoxy-5-(2-oxo-1,2-dihydro-pyridin-3-yl)-phenyl]-2-fluoro-4-hydroxy-benzamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

step 2—To a solution of 322 (88 mg, 0.171 mmol) and HOAc (3 mL) in a 2-5 mL microwave tube was added 48% HBr (0.037 mL, 0.684 mmol). The tube was sealed and heated to 60° for 4 h then to 40° overnight. The reaction was still incomplete so heating at was continued for 6 h at 70°. The reaction was cooled to RT, concentrated and stirred with dilute aq. K2CO3, then twice extracted with EtOAc, dried (MgSO4), filtered and concentrated. The crude product was purified on a SiO2 TLC plate developed with 75% EtOAc/hexane to afford 25 mg (965%) of I-252 as a white solid: MS (M+H)=411.

Workup

  1. customThe tube was sealed
  2. temperatureheated to 60° for 4 h
  3. customto 40°
  4. customovernight
  5. temperatureso heating
  6. concentrationconcentrated
  7. extractiontwice extracted with EtOAc
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified on a SiO2 TLC plate
  12. customto afford 25 mg (965%) of I-252 as a white solid

Sources & evidence

ORD record
ord-dc43d34604bf4047b3aa75c65b71d840
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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