Water → 6-chloro-4-(4-fluoro-1H-indol-2-yl)nicotinaldehyde

HRID 595726Notes

Reaction equation

HRID 595726 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:11])CO)=[C:4]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[C:18]([F:21])[CH:17]=[CH:16][CH:15]=3)[CH:3]=1.[O-]S([O-])=O.[Na+].[Na+].O>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[C:18]([F:21])[CH:17]=[CH:16][CH:15]=3)[C:5]([CH:8]=[O:11])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24437Sodium SulfiteHCID 903336091-(6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)ethane-1,2-diol

Product 1

HCID 903335666-chloro-4-(4-fluoro-1H-indol-2-yl)nicotinaldehydeYield 82.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 1-(6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)ethane-1,2-diol (1.9 g, 6.21 mmol) in THF—H2O (26 mL-13 mL), NaIO4 (1.94 g, 9.31 mmol) was added, the reaction mixture was stirred at room temperature for 2 hours. Then Na2SO3 and water were added and the mixture was stirred at room temperature for 30 min. The mixture was extracted with EA. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography (DCM:MeOH=20:1) to afford the desired product of 6-chloro-4-(4-fluoro-1H-indol-2-yl)nicotinaldehyde (1.4 g, yield: 82.4%). 1H-NMR (Methanol-d4, 400 MHz) δ 8.48 (s, 1H), 7.79 (s, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.17˜7.25 (m, 1H), 6.95 (s, 1H), 6.79 (dd, J=8.0, 10.0 Hz, 1H), 6.70 (s, 1H). MS (M+H)+: 275/277.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. extractionThe mixture was extracted with EA
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (DCM:MeOH=20:1)

Sources & evidence

ORD record
ord-ee716b6735f744af941a80f3d356d418
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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