HCID 86676383, compound → HCID 86724187, compound

HRID 873151Notes

Reaction equation

HRID 873151 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=2[F:17])[CH:5]=[CH:4][N:3]=1.[C:18]([Zn]C#N)#[N:19]>CN(C)C(=O)C.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>[F:17][C:10]1[CH:11]=[C:12]([CH:13]=[O:14])[CH:15]=[CH:16][C:9]=1[O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:18]#[N:19])[CH:7]=1

Participants

5

Reactant 2

HCID 86676383HCID 86676383, compoundHCID 178514179HCID 178514179, compound

Product 1

HCID 86724187HCID 86724187, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-((2-chloropyridin-4-yl)oxy)-3-fluorobenzaldehyde (580 mg, 2.31 mmol) and dicyanozinc (271 mg, 2.31 mmol) in N,N-dimethylacetamide (DMA) (4 mL) was added tetrakis(triphenylphosphine)palladium(0) (266 mg, 0.230 mmol). The reaction mixture was sealed in a microwave vial and irradiated with a microwave using initial normal to 100° C. for 1 h, and then filtered. Direct purification via reversed phase chromatography (acetonitrile/water: 5%-95%, 0.25% NH4OH) afforded the title product (170 mg) as a white solid.

Workup

  1. customThe reaction mixture was sealed in a microwave vial
  2. customirradiated with a microwave
  3. customnormal to 100° C.
  4. customfor 1 h
  5. filtrationfiltered
  6. customDirect purification

Sources & evidence

ORD record
ord-095e9167e2b3405586a11afdc525e160
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

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