1,1-Dichloroethane → 4-[(6-Chloro-2-fluoropyridin-3-yl)methyl]thiomorpholine 1,1-dioxide

HRID 386016Notes

Reaction equation

HRID 386016 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[N:3]=1.ClC(Cl)C.[NH:15]1[CH2:20][CH2:19][S:18](=[O:22])(=[O:21])[CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>>[Cl:1][C:2]1[N:3]=[C:4]([F:10])[C:5]([CH2:6][N:15]2[CH2:20][CH2:19][S:18](=[O:22])(=[O:21])[CH2:17][CH2:16]2)=[CH:8][CH:9]=1

Participants

6

Reactant 5

HCID 63651,1-DichloroethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 6484228Thiomorpholine 1,1-dioxideHCID 510407866-Chloro-2-fluoronicotinaldehyde

Product 1

HCID 595257164-[(6-Chloro-2-fluoropyridin-3-yl)methyl]thiomorpholine 1,1-dioxide

Procedure

6-Chloro-2-fluoronicotinaldehyde (116 mg, 0.73 mmol) was added to a 200 mL round bottom under argon. Dichloroethane (2.9 ml) was added followed by thiomorpholine 1,1-dioxide (98 mg, 0.73 mmol). The mixture was stirred for 45 min at room temperature, at which time sodium triacetoxyborohydride (216 mg, 1.02 mmol) was added. The resulting slurry was stirred for 72 hours at room temperature. Saturated aqueous sodium bicarbonate was added and the resulting mixture was extracted twice with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (silica, 0-100% ethyl acetate/hexanes) to afford the title compound.

Workup

  1. additionwas added
  2. extractionthe resulting mixture was extracted twice with ethyl acetate
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash chromatography (silica, 0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ad41fafc84d8448cac19392f4ca0b7d9
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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