Dimethylformamide → HCID 67547360, compound

HRID 2089489Notes

Reaction equation

HRID 2089489 reaction equation
I[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][S:8][CH2:9]2)=[CH:4][CH:3]=1.[CH3:13][N:14](C=O)C>[C-]#N.[C-]#N.[Zn+2].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>[O:12]=[C:6]1[C:5]2[C:10](=[CH:11][C:2]([C:13]#[N:14])=[CH:3][CH:4]=2)[CH2:9][S:8][CH2:7]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 59199322HCID 59199322, compound

Product 1

HCID 67547360HCID 67547360, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
95 °C

Procedure

To a solution of 7-iodo-isothiochroman-4-one (290 mg, 1.0 mmol) in DMF (5 mL) is added Zn(CN)2 (117 mg, 1.0 mmol) and Pd(PPh3)4 (124 mg, 0.1 mmol). The reaction is then heated to 95° C. for 3 hours, at which time it is cooled to room temperature and concentrated to dryness. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 1:10 to 3:10) to furnish 4-oxo-isothiochroman-7-carbonitrile; MS: (ESI) m/z 188.2 (M−H)−.

Workup

  1. temperatureis cooled to room temperature
  2. concentrationconcentrated to dryness
  3. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 1:10 to 3:10)

Sources & evidence

ORD record
ord-7b05f57a45c748109010f44c1c4541eb
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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