Sodium hydride → HCID 178525771, compound

HRID 1670662Notes

Reaction equation

HRID 1670662 reaction equation
[CH2:1]1[CH:6]([C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH:3]([OH:10])[CH2:2]1.[H-].[Na+].[Br:13][C:14]1[CH:15]=[CH:16][C:17](F)=[N:18][CH:19]=1>CC(N(C)C)=O>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([O:10][C@@H:3]2[CH2:4][CH2:5][C@H:6]([C:7]([OH:9])=[O:8])[CH2:1][CH2:2]2)=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1511384-Hydroxycyclohexanecarboxylic acidHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 178525771HCID 178525771, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent3×

Conditions

Temperature
100 °C

Procedure

A solution of (1S,4S)-4-hydroxycyclohexanecarboxylic acid (2.14 g, 14.9 mmol) in DMA (10 mL) was added to a stirred suspension of NaH (1.32 g, 30.2 mmol) in DMA (15 mL) at 0° C. where it was stirred for 10 min. The suspension was taken off the cooling bath and 5-bromo-2-fluoropyridine (1.53 mL, 14.87 mmol, CAS 766-11-0) was added followed by DMA (10 mL). The reaction was heated at 100° C. for 2.5 h. The solvent was evaporated and DCM and 2M HCl were added, the phases separated and the aqueous phase was extracted with DCM (2×50 mL). The combined organics were dried over MgSO4, filtered and evaporated. The remaining crude was purified by flash chromatography using 5-75% EtOAc (1% HOAc) in heptane to afford the title compound (1.86 g, 42%) as solid.

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. additionDCM and 2M HCl were added
  4. customthe phases separated
  5. extractionthe aqueous phase was extracted with DCM (2×50 mL)
  6. dry with materialThe combined organics were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe remaining crude was purified by flash chromatography

Sources & evidence

ORD record
ord-934755b5777d4606be214aff355b785f
Source dataset
uspto-grants-2011_08
Patent number
US07994179B2

Reaction notes

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