Dimethylformamide → 3-(Azidomethyl)-2-(3-fluorophenyl)-8-methoxyquinoline

HRID 1397769Notes

Reaction equation

HRID 1397769 reaction equation
Cl.Cl[CH2:3][C:4]1[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[O:14][CH3:15].CN(C=O)C.[N-:28]=[N+:29]=[N-:30].[Na+]>>[N:28]([CH2:3][C:4]1[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[O:14][CH3:15])=[N+:29]=[N-:30]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 689445683-(Chloromethyl)-2-(3-fluorophenyl)-8-methoxyquinoline hydrochloride

Product 1

HCID 866700723-(Azidomethyl)-2-(3-fluorophenyl)-8-methoxyquinoline

Procedure

To a stirring solution of 3-(chloromethyl)-2-(3-fluorophenyl)-8-methoxyquinoline hydrochloride (0.9601 g, 2.839 mmol) in DMF (14.19 mL, 2.839 mmol) was added sodium azide (0.3691 g, 5.678 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 (100 mL×1), dried over Na2SO4, filtered, and concentrated under reduced pressure to give 3-(azidomethyl)-2-(3-fluorophenyl)-8-methoxyquinoline as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.48 (1 H, s), 7.54-7.62 (3 H, m), 7.43-7.49 (2 H, m), 7.32-7.39 (1 H, m), 7.21-7.28 (1 H, m), 4.68 (2 H, s), 3.97 (3 H, s); LC-MS (ESI) m/z 309.1 [M+H]+. The yellow solid was carried on crude without purification for the next step.

Workup

  1. customthe mixture was partitioned between EtOAc (100 mL) and H2O (100 mL)
  2. washThe organic layer was washed with brine (100 mL×1)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-517d06726d784d8985f9071aa6c8fd4c
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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