Water → 1-(6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)ethane-1,2-diol

HRID 595725Notes

Reaction equation

HRID 595725 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[C:14]([F:17])[CH:13]=[CH:12][CH:11]=3)[C:5]([CH:18]=[CH2:19])=[CH:4][N:3]=1.C[N+]1([O-])CC[O:24]CC1.[O-]S([O-])=O.[Na+].[Na+].[OH2:34]>C1COCC1.O.O=[Os](=O)(=O)=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:18]([OH:24])[CH2:19][OH:34])=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[C:14]([F:17])[CH:13]=[CH:12][CH:11]=3)[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 903335672-(2-chloro-5-vinylpyridin-4-yl)-4-fluoro-1H-indole

Product 1

HCID 903336091-(6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)ethane-1,2-diolYield 84.4%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 2-(2-chloro-5-vinylpyridin-4-yl)-4-fluoro-1H-indole (2 g, 7.35 mmol) in THF—H2O (26 mL-13 mL), NMO (2.15 g, 18.38 mmol) and OsO4 (56 mg, 0.22 mmol) were added. The reaction mixture was stirred at room temperature for 2 hours. Then Na2SO3 and water were added. The mixture was stirred at room temperature for 20 min and filtered. The filtrate 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=10:1) to give 1-(6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)ethane-1,2-diol (1.9 g, yield: 84.4%). 1H-NMR (Methanol-d4, 400 MHz) 8.61 (s, 1H), 7.63 (s, 1H), 7.24 (d, J=8.0 Hz, 1H), 7.08˜7.19 (m, 1H), 6.90 (s, 1H), 6.75 (dd, J=7.6, 10.0 Hz, 1H), 5.19 (t, J=6.0 Hz, 1H), 3.75˜3.82 (m, 1H), 3.67˜3.74 (m, 1H). MS (M+H)+: 307/309.

Workup

  1. stirringThe mixture was stirred at room temperature for 20 min
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with EA
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (DCM:MeOH=10:1)

Sources & evidence

ORD record
ord-b177e5be09fa4c7081d9afbdd8b0b88c
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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