Dichloromethane → HCID 131730948, compound

HRID 2035493Notes

Reaction equation

HRID 2035493 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[O:10])=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)[CH:3]=1.[O:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=2)[CH2:24][CH2:23]1.ClCCl.CC(C)([O-])C.[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:21][C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([F:20])[CH:17]=1)[CH2:13][NH:12][C:4]1[CH:3]=[C:2]([NH:32][C:31]2[CH:33]=[CH:34][C:28]([CH:25]3[CH2:24][CH2:23][O:22][CH2:27][CH2:26]3)=[CH:29][CH:30]=2)[N:7]=[CH:6][C:5]=1[CH2:8][C:9]([NH2:11])=[O:10]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 203654724-(Oxan-4-yl)anilineHCID 23676156Sodium t-butoxideHCID 1317309496-Chloro-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide

Product 1

HCID 131730948HCID 131730948, compoundYield 16.6%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

29 mg of 6-chloro-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (the compound of Example 20) and 35 mg of 4-(tetrahydro-2H-pyran-4-yl)aniline were dissolved in 0.35 mL of 1,4-dioxane, to which 8.0 mg of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane, 17 mg of 1,1′-bis (diphenylphosphino)ferrocene and 12 mg of sodium tert-butoxide were added, and stirred using a microwave reaction apparatus under an argon atmosphere at 100° C. for 1 hour. After cooling, the solvent was evaporated and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=20:1) to obtain 7 mg (16%) of the title compound as a white crystalline powder.

Workup

  1. additionwere added
  2. customa microwave reaction apparatus under an argon atmosphere at 100° C. for 1 hour
  3. temperatureAfter cooling
  4. customthe solvent was evaporated
  5. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-7e140799b5dc43d08ba11f856b05cf4f
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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