tert-Butyl (2,6-dichloropyridin-4-yl)carbamate → HCID 77231196, compound

HRID 1039064Notes

Reaction equation

HRID 1039064 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[C:4]([Cl:16])[N:3]=1.[CH3:17][Mg]Br>C1COCC1.CN1C(=O)CCC1>[Cl:16][C:4]1[CH:5]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=[C:2]([CH3:17])[N:3]=1

Participants

4

Reactant 2

HCID 45076485tert-Butyl (2,6-dichloropyridin-4-yl)carbamateHCID 178418573HCID 178418573, compound

Product 1

HCID 77231196HCID 77231196, compound

Reagents, catalysts & solvents 1

HCID 22156051tetrahydrofuran N-methylpyrrolidinoneSolvent

Procedure

tert-butyl (2,6-dichloropyridin-4-yl)carbamate (460 mg, 1.75 mmol) from Step 1 of this example, ferric acetylacetonate (309 mg, 0.87 mmol) was added in THF:NMP (1:1, 17.4 mL), methyl magnesium bromide (3 mL [3M], 8.9 mmol) was added drop-wise and stirred for 15 min. The reaction was quenched with ice-cold ammonia chloride saturated solution (100 mL), extracted with ethyl acetate (100 mL), second wash with brine (50 mL). The organic phase was dried by magnesium sulfate and filtered through silica gel (1 inch deep), concentrated and purified by column chromatography through a 50 gram Biotage SNAP KP-Sil™ silica gel cartridge eluting with 10% ethyl acetate/hexanes to give the title compounds as a white solid.

Workup

  1. customThe reaction was quenched with ice-cold ammonia chloride saturated solution (100 mL)
  2. extractionextracted with ethyl acetate (100 mL)
  3. washsecond wash with brine (50 mL)
  4. dry with materialThe organic phase was dried by magnesium sulfate
  5. filtrationfiltered through silica gel (1 inch deep)
  6. concentrationconcentrated
  7. custompurified by column chromatography through a 50 gram Biotage SNAP KP-Sil™ silica gel cartridge
  8. washeluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-94126aea81d14cd6be55466919ab2222
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

Loading…