Dimethylformamide → HCID 57471182, compound

HRID 1044485Notes

Reaction equation

HRID 1044485 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][CH2:21][CH3:22])=[O:19])[CH:10]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=3)[C:9]=2[CH:8]=1)(=O)=O.[CH3:34][N:35](C)C=O>[C-]#N.[Zn+2].[C-]#N>[C:34]([C:7]1[CH:8]=[C:9]2[C:14]([CH2:13][CH2:12][CH:11]([NH:17][C:18](=[O:19])[O:20][CH2:21][CH3:22])[CH:10]2[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)=[CH:15][CH:16]=1)#[N:35]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 46870536HCID 46870536, compound

Product 1

HCID 57471182HCID 57471182, compound

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

8-(3,4-Dichlorobenzyl)-7-[(ethoxycarbonyl)amino]-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (250 mg, 0.475 mmol), zinc cyanide (139 mg, 1.187 mmol) and tetrakistriphenyl palladium (82 mg, 0.071 mmol) in dimethylformamide (5 mL) were heated in the microwave at 120° C. (100 W) under stirring for 35 min. The solvent was evaporated in vacuo and the crude product was partitioned between ethyl acetate (40 mL) and water (30 mL). The aqueous layer was extracted with ethyl acetate one more time (20 mL) and the combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The crude product (460 mg) was purified by flash chromatography (dichloromethane to dichloromethane:methanol=100:1, silica gel). Yield: 109 mg (0.270 mmo, 57%, colorless solid).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude product was partitioned between ethyl acetate (40 mL) and water (30 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate one more time (20 mL)
  4. dry with materialthe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product (460 mg) was purified by flash chromatography (dichloromethane to dichloromethane:methanol=100:1, silica gel)

Sources & evidence

ORD record
ord-fadbaa702dc34899bf90777c580c6948
Source dataset
uspto-grants-2013_10
Patent number
US08563617B2

Reaction notes

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