Dimethylformamide → HCID 24765407, compound

HRID 1255124Notes

Reaction equation

HRID 1255124 reaction equation
Br[C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([C:11]2[S:15][C:14]([NH:16][C:17](=[O:26])[C:18]3[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=3[F:25])=[N:13][C:12]=2[CH3:27])[CH:3]=1.[CH3:28][N:29](C=O)C>C(OCC)(=O)C.[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:28]([C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([C:11]2[S:15][C:14]([NH:16][C:17](=[O:26])[C:18]3[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=3[F:25])=[N:13][C:12]=2[CH3:27])[CH:3]=1)#[N:29]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 24765405N-(5-(7-Bromobenzo[d][1,3]dioxol-5-yl)-4-methylthiazol-2-yl)-2,6-difluorobenzamide

Product 1

HCID 24765407HCID 24765407, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A degassed mixture of Compound 56 (80 mg, 0.18 mmol), zinc cyanide (26 mg, 0.22 mmol) and tetrakis(triphenylphosphine)palladium (20.0 mg, 0.017 mmol) in DMF (2.0 mL) was heated to 100° C. overnight. The mixture was cooled to room temperature, diluted with ethyl acetate. The mixture was washed with a solution of saturated NaHCO3 then with brine, dried (Na2SO4), filtered and concentrated. The residue was purified on silica to provide Compound 58 (55 mg).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washThe mixture was washed with a solution of saturated NaHCO3
  3. dry with materialwith brine, dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica

Sources & evidence

ORD record
ord-ba6a557094f04c3688ab46c12cb7dc7f
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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