Isopropylamine → HCID 86672646, compound

HRID 1530209Notes

Reaction equation

HRID 1530209 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH:13]([NH2:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([NH:16][CH:13]([CH3:15])[CH3:14])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 10796Cesium carbonateHCID 93237Methyl 2,6-dichloroisonicotinateHCID 634876Binap, (A+-)-

Product 1

HCID 86672646HCID 86672646, compoundYield 27.27%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of methyl 2,6-dichloroisonicotinate (1 g, 4.85 mmol), isopropyl amine (0.286 g, 4.85 mmol), Cs2CO3 (2.06 g, 6.3 mmol) in toluene (30 mL) was purged with argon for 10 min. Then, Pd(OAc)2 (0.108 g, 0.485 mmol) and BINAP (0.3 g, 0.485 mmol) were added and argon was purged again for 15 min. Reaction mass was stirred at 80° C. for 6 h. On completion, reaction mass was filtered and residue washed thoroughly with ethyl acetate. Combined filtrates were concentrated and purified by column over silica gel to obtain pure methyl 2-chloro-6-(isopropylamino)isonicotinate (0.3 g, 27.27%).

Workup

  1. customargon was purged again for 15 min
  2. customReaction mass
  3. customOn completion, reaction mass
  4. filtrationwas filtered
  5. washresidue washed thoroughly with ethyl acetate
  6. concentrationCombined filtrates were concentrated
  7. custompurified by column over silica gel

Sources & evidence

ORD record
ord-837caaee62ca4541bc81630d3527598c
Source dataset
uspto-grants-2015_07
Patent number
US09090562B2

Reaction notes

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