Sodium Chloride → HCID 69707693, compound

HRID 396365Notes

Reaction equation

HRID 396365 reaction equation
[CH:1](NC(C)C)([CH3:3])[CH3:2].[Li]CCCC.[F:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=1.[F:21]C1C=CC(C(N(OC)C)=O)=CC=1.[Na+].[Cl-].[CH2:36]1[CH2:40][O:39][CH2:38][CH2:37]1>CCCCCC>[F:21][C:18]1([CH2:20][C:38]([C:37]2[CH:36]=[CH:40][CH:3]=[CH:1][CH:2]=2)=[O:39])[CH:17]=[CH:16][N:15]=[C:14]([F:13])[CH2:19]1

Participants

8

Reactant 6

HCID 5234Sodium ChlorideHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 27374032-Fluoro-4-methylpyridineHCID 140693474-Fluoro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 69707693HCID 69707693, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Diisopropylamine (0.93 ml; 6.55 mmol) in THF (6 ml) is cooled to −78 C. and treated with nBuLi (3.8 ml; 6.08 mmol of a 1.6 M solution in hexane). 2-Fluoro-4-methylpyridine (620 mg; 5.4 mmol) is added dropwise and stirred under argon for 30 min. 4-Fluoro-N-methoxy-N-methylbenzamide (1 g; 5.46 mmol) is added dropwise in THF (0.5 ml) and the reaction mixture allowed to warm up to room temperature within 10 min. then poured on a saturated solution of NaCl and extracted with TBME three times. The combined organic phases are washed with water, dried over Na2SO4, filtered and evaporated to dryness to yield the title compound as pale yellow crystals. Purification by recrystallisation from hot TBME rendered the desired compound as white solid (630 mg; 50%).

Workup

  1. extractionextracted with TBME three times
  2. washThe combined organic phases are washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-8f6898596f474688a796c1605402e14b
Source dataset
uspto-grants-2003_08
Patent number
US06608072B1

Reaction notes

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