Dimethylformamide → HCID 131733316, compound

HRID 515903Notes

Reaction equation

HRID 515903 reaction equation
[CH3:1][N:2](C)C=O.[Si:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23](Cl)[N:22]=2)=[CH:16][CH:15]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]>[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.O>[Si:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]([C:1]#[N:2])[N:22]=2)=[CH:16][CH:15]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 131733315HCID 131733315, compound

Product 1

HCID 131733316HCID 131733316, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Anhydrous N,N-dimethylformamide (10 mL) is placed under nitrogen in a flask and then the compound of Step A (670 mg, 2.0 mmol) is added. Zinc cyanide (468 mg, 4.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (404 mg, 0.3 mmol) are subsequently added. Nitrogen is bubbled through the solution for 5 minutes and then the reaction mixture is stirred at 120° C. for 2 hours under a nitrogen atmosphere. The reaction, monitored by LC-MS, is complete. The mixture is cooled to ambient temperature, and then water (15 mL) is added thereto. The product is extracted with AcOEt (3×25 mL). The organic phases are combined and washed with water (4×25 mL), and then with brine (1×25 mL). The organic phase is dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by chromatography over silica gel using ethyl acetate and heptane as eluants to obtain the expected compound in the form of a solid.

Workup

  1. customNitrogen is bubbled through the solution for 5 minutes
  2. customThe reaction
  3. temperatureThe mixture is cooled to ambient temperature
  4. extractionThe product is extracted with AcOEt (3×25 mL)
  5. washwashed with water (4×25 mL)
  6. dry with materialThe organic phase is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by chromatography over silica gel

Sources & evidence

ORD record
ord-62ee1b0b3dd34b40b7ab05cd7220b2f8
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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