Dimethylformamide → HCID 57471190, compound

HRID 510505Notes

Reaction equation

HRID 510505 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH:11]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:10]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:9]=2[CH:8]=1)(=O)=O.[CH3:35][N:36](C)C=O>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.[Fe+2].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].[C-]#N.[Zn+2].[C-]#N>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][CH:10]2[C:9]3[C:14](=[CH:15][CH:16]=[C:7]([C:35]#[N:36])[CH:8]=3)[CH2:13][CH2:12][CH:11]2[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:27][CH:28]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 574672047-(Tert-butoxycarbonylamino)-8-(4-chlorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 57471190HCID 57471190, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
90 °C

Procedure

DPPF (8.1 mg, 0.015 mmol) and Pd2dba3 (3.35 mg, 0.00365 mmol) were suspended in dimethylformamide (0.4 mL) and after stirring at room temperature under an inert atmosphere of nitrogen for 20 min 7-[(tert-butoxycarbonyl)amino]-8-(4-chlorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (38 mg, 0.073 mmol) and zinc cyanide (12.87 mg, 0.110 mmol) were added. The reaction mixture was stirred at 90° C. for 1 h. The solvent was evaporated in vacuo. Water (10 mL) was added to the crude product and the aqueous layer was extracted with ethyl acetate (two times with 10 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash chromatography (dichloromethane, silica gel). Yield: 16 mg (0.040 mmol, 55%).

Workup

  1. additionwere added
  2. customThe solvent was evaporated in vacuo
  3. additionWater (10 mL) was added to the crude product
  4. extractionthe aqueous layer was extracted with ethyl acetate (two times with 10 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (dichloromethane, silica gel)

Sources & evidence

ORD record
ord-ebdc457dbddd4cc3abfe52f82cbc35f5
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

Loading…