Salicylaldehyde oxime → HCID 68426651, compound

HRID 499004Notes

Reaction equation

HRID 499004 reaction equation
[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:9][C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1[OH:17])[CH3:8])([CH3:4])([CH3:3])[CH3:2].Br[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1.C([O-])([O-])=O.[Cs+].[Cs+].C(=NO)C1C(=CC=CC=1)O>C(Cl)Cl.CN(C=O)C>[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:9][C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1[O:17][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 7200Salicylaldehyde oximeHCID 79732-BromopyridineHCID 10796Cesium carbonateHCID 68427594HCID 68427594, compound

Product 1

HCID 68426651HCID 68426651, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (5-bromo-2-hydroxy-benzyl)-methyl-carbamic acid tert-butyl ester (581 mg, 1.22 mmol), 2-bromopyridine (238 μL, 2.44 mmol), Cs2CO3 (795 mg, 2.44 mmol), powdered 3 Å molecular sieves (366 mg), salicylaldoxime (33.5 mg, 0.244 mmol), Ca2O (9 mg, 0.06 mmol), and DMF (3 mL) was heated at 100° C. for 24 h. After cooling to rt, the mixture was diluted with DCM, filtered through diatomaceous earth, and concentrated. FCC purification (EtOAc/hexanes) gave the desired product (321 mg, 67%). 1H NMR (CDCl3, mixture of rotamers): 8.17-8.12 (m, 1H), 7.74-7.66 (m, 1H), 7.44-7.38 (m, 2H), 7.04-6.90 (m, 3H), 4.44-4.32 (m, 2H), 2.88-2.75 (m, 3H), 1.52-1.40 (m, 9H).

Workup

  1. temperatureAfter cooling to rt
  2. filtrationfiltered through diatomaceous earth
  3. concentrationconcentrated
  4. customFCC purification (EtOAc/hexanes)

Sources & evidence

ORD record
ord-358d009fe5ea4609a3387ebe0509a83a
Source dataset
uspto-grants-2010_08
Patent number
US07767666B2

Reaction notes

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