Hydrochloric Acid → HCID 58925884, compound

HRID 509273Notes

Reaction equation

HRID 509273 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][C@@H:11]1[CH2:16][NH:15][CH2:14][CH2:13][NH:12]1.CC(C)([O-])C.[Na+].Cl>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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.CO>[CH3:10][C@H:11]1[NH:12][CH2:13][CH2:14][N:15]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:16]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 12162Benzonitrile, 4-bromo-HCID 73304342-Methylpiperazine, (R)-HCID 23676156Sodium t-butoxide

Product 1

HCID 58925884HCID 58925884, compoundYield 69%

Reagents, catalysts & solvents 4

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromobenzonitrile (200 mg, 1.099 mmol), (R)-2-methylpiperazine (121 mg, 1.209 mmol), Pd2(dba)3 (20 mg, 0.022 mmol), BINAP (41 mg, 0.066 mmol), and sodium-tert-butoxide (211 mg, 2.199 mmol) were suspended in toluene (5 ml), and then the resulting liquid was stirred at 100° C. under nitrogen stream for 5 hours. 1N aqueous HCl solution (20 ml) was added to the resulting reaction liquid, followed by extraction with MC (10 ml×2). The aqueous layer was neutralized by addition of 5N aqueous NaOH solution, followed by extraction with 5% MeOH/MC (20 ml×2). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (10% MeOH/MC), to obtain 152 mg of pale yellow oil (69%).

Workup

  1. extractionfollowed by extraction with MC (10 ml×2)
  2. additionThe aqueous layer was neutralized by addition of 5N aqueous NaOH solution
  3. extractionfollowed by extraction with 5% MeOH/MC (20 ml×2)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfollowed by filtration and concentration
  6. customthe residue thus obtained

Sources & evidence

ORD record
ord-3d4c2eb268ea4bf88e5d91d7d5eb95aa
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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