Dimethylformamide → HCID 59191329, compound

HRID 626021Notes

Reaction equation

HRID 626021 reaction equation
N1[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].ClCC1[CH:23]=[CH:22][C:13]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[N:16]=2)=[C:12]([O:24][CH3:25])[CH:11]=1.[CH3:26][N:27](C=O)[CH3:28]>>[F:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][C:13]2[CH:22]=[CH:23][C:5]([CH2:4][N:3]3[CH:28]=[N:27][CH:26]=[N:2]3)=[CH:11][C:12]=2[O:24][CH3:25])[N:16]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 59191250HCID 59191250, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 59191329HCID 59191329, compound

Conditions

Temperature
40 °C

Procedure

To a solution of triazole (18 mg; 0.267 mmol) and NaH (10 mg; 0.25 mmol) in DMF (1 mL), under argon, was added a solution of 2-[4-(chloromethyl)-2-methoxyphenoxy]-6-fluoropyridine (65 mg; 0.243 mmol) in DMF (1 mL). The reaction mixture was allowed to stir overnight at 40° C. After concentration, the reaction was hydrolysed with saturated NH4Cl (1 mL), extracted with AcOEt (2*1 mL). Combined organic phases were dried over Na2SO4, concentrated in vacuo, the title compound (72 mg; quantitative) was obtained.

Workup

  1. concentrationAfter concentration
  2. extractionextracted with AcOEt (2*1 mL)
  3. dry with materialCombined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c740ac4522ba41eb8ffe4e1c4ff7f385
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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