Sodium hydride → HCID 86691232, compound

HRID 2038217Notes

Reaction equation

HRID 2038217 reaction equation
[H-].[Na+].[NH2:3][CH2:4][C@H:5]([OH:9])[CH2:6][O:7][CH3:8].F[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=1>CC(N(C)C)=O>[F:17][C:14]1[CH:15]=[CH:16][C:11]([O:9][C@H:5]([CH2:6][O:7][CH3:8])[CH2:4][NH2:3])=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1891103(S)-1-Amino-3-methoxy-propan-2-olHCID 27628712,5-Difluoropyridine

Product 1

HCID 86691232HCID 86691232, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

Suspend sodium hydride (60% in mineral oil, 13.56 g, 339.1 mmol) in dimethylacetamide (245.7 mL) and add a solution of (2S)-1-amino-3-methoxy-2-propanol (31.0 g, 147.4 mmol) in dimethylacetamide (59.0 mL) over 30 minutes. Stir for one hour; then add 2,5-difluoropyridine (17.03 mL, 162.17 mmol) over a 30 min interval; and stir at ambient temperature for an additional 1.5 hours. Slowly add water (930 mL) to quench the reaction. Extract the resulting mixture with EtoAc (4×300 mL) and combine the organic extracts. Dry the combined extracts over magnesium sulfate; filter and concentrate the filtrate under reduced pressure. Purify via flash column chromatography using a gradient of 0 to 10% EtOAc in DCM to give the title compound as a brown oil (12.0 g). MS (m/z): 201 (M+1).

Workup

  1. stirringand stir at ambient temperature for an additional 1.5 hours
  2. customSlowly add water (930 mL) to quench
  3. customthe reaction
  4. extractionExtract the resulting mixture with EtoAc (4×300 mL)
  5. dry with materialDry the combined extracts over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate the filtrate under reduced pressure
  8. customPurify via flash column chromatography

Sources & evidence

ORD record
ord-3be68ea9eebc4e4ca08911a16ab7ccbe
Source dataset
uspto-grants-2013_11
Patent number
US08575352B2

Reaction notes

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