Dimethylformamide → HCID 15979314, compound

HRID 656480Notes

Reaction equation

HRID 656480 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][CH2:13][C:14]32[CH2:21][CH2:20][CH2:19][N:18]2[CH:22]=[N:23][CH:24]=[C:17]32)=[CH:9][CH:8]=1)(=O)=O.[CH3:27][N:28](C)C=O>[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:14]12([CH2:21][CH2:20][CH2:19][N:18]3[CH:22]=[N:23][CH:24]=[C:17]13)[C:15]1[C:10](=[CH:9][CH:8]=[C:7]([C:27]#[N:28])[CH:16]=1)[CH2:11][CH2:12][CH2:13]2

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 86637924HCID 86637924, compound

Product 1

HCID 15979314HCID 15979314, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

An apparatus purified by baking is charged under argon with 1.160 mmol of 3′,4′,6,7-tetrahydro-2′H,5H-spiro[imidazo[1,5-a]pyridine-8,1′-naphthalen]-7′-yl trifluoromethanesulphonate together with 2.320 mmol zinc(II) cyanide in 15 ml of degassed N,N-dimethylformamide. 0.093 mmol of tetrakis(triphenylphosphine)palladium is added and the reaction mixture is stirred at 120° C. for 20 hours. The reaction mixture is cooled and poured into 100 ml of ice-water. It is extracted with ethyl acetate (3×). The combined organic phases are dried over magnesium sulphate and evaporated. From the residue the title compound is obtained by means of flash chromatography (SiO2 60F) as a white solid. Rf=0.165 (dichloromethane-2M ammonia in EtOH=95:5); Rt=5.64.

Workup

  1. customAn apparatus purified by baking
  2. temperatureThe reaction mixture is cooled
  3. extractionIt is extracted with ethyl acetate (3×)
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-0b911a8441a34abeb6ab870782e2a66c
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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