Dimethylformamide → HCID 86670071, compound

HRID 2044924Notes

Reaction equation

HRID 2044924 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:20]([F:23])([F:22])[F:21])[C:9]([CH2:24]Cl)=[CH:8]2.CN(C=O)C.[N-:31]=[N+:32]=[N-:33].[Na+]>>[N:31]([CH2:24][C:9]1[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][C:20]([F:23])([F:22])[F:21])=[N:11][C:12]2[C:7]([CH:8]=1)=[CH:6][CH:5]=[CH:4][C:3]=2[Cl:2])=[N+:32]=[N-:33]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 86630637HCID 86630637, compound

Product 1

HCID 86670071HCID 86670071, compound

Procedure

To a stirring solution of 8-chloro-3-(chloromethyl)-2-(2-(trifluoromethoxy)-phenyl)quinoline hydrochloride (0.6319 g, 1.546 mmol) in DMF (7.732 mL, 1.546 mmol) was added sodium azide (0.2011 g, 3.093 mmol) at room temperature and the mixture was stirred at room temperature. After 1 h, the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL). The organic layer was washed with brine (50 mL×1), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography on a 40 g of Redi-Sep™ column using 0 to 50% gradient of EtOAc in hexane over 14 min, then 50% isocratic of EtOAc for 5 min as eluent to give 3-(azidomethyl)-8-chloro-2-(2-(trifluoromethoxy)phenyl)quinoline as a colorless syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.66 (1 H, s), 8.11 (1 H, dd, J=8.2, 1.2 Hz), 8.02 (1 H, dd, J=7.6, 1.4 Hz), 7.54-7.74 (5 H, m), 4.52 (2 H, br. s.); LC-MS (ESI) m/z 379.0 [M+H]+.

Workup

  1. customthe mixture was partitioned between EtOAc (100 mL) and H2O (100 mL)
  2. washThe organic layer was washed with brine (50 mL×1)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography on a 40 g of Redi-Sep™ column
  7. customover 14 min

Sources & evidence

ORD record
ord-45c8089a34564921b2ed76ef535add33
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

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