Dimethylformamide → HCID 67305526, compound

HRID 535111Notes

Reaction equation

HRID 535111 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH:22]=2)[CH:5]=[C:6]([CH3:16])[C:7]=1OS(C(F)(F)F)(=O)=O.[CH3:30][N:31](C)C=O>CCOCC.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:30]([C:7]1[C:2]([CH3:1])=[CH:3][C:4]([C:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH:22]=2)=[CH:5][C:6]=1[CH3:16])#[N:31]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 86598269HCID 86598269, compound

Product 1

HCID 67305526HCID 67305526, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl 4-(3,5-dimethyl-4-[(trifluoromethyl)sulfonyl]oxyphenyl)-3,6-dihydropyridine-1(2H)-carboxylate (2.80 g, 0.00643 mol) and zinc cyanide (1.51 g, 0.0128 mol) in N,N-dimethylformamide (15.0 mL, 0.194 mol)was degassed with nitrogen for 15 min. To the mixture was added tetrakis(triphenylphosphine)palladium(0) (0.74 g, 0.00064 mol). The reaction mixture was heated at 100 Celsius for 4 h. The mixture was diluted with ether, washed with aq. sodium bicarbonate, brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified on silica gel, eluting with 0 to 10% EtOAc in hexane, to generate the titled compound (1.08 g, 53.66%). LCMS (M+H) 313.1

Workup

  1. customwas degassed with nitrogen for 15 min
  2. washwashed with aq. sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified on silica gel
  6. washeluting with 0 to 10% EtOAc in hexane

Sources & evidence

ORD record
ord-24d70a4478674976a810a9f73c03ad01
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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