HCID 22136198, compound → HCID 10172758, compound

HRID 1826705Notes

Reaction equation

HRID 1826705 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:12]=[C:11](I)[CH:10]=2)=[O:7])=[CH:4][CH:3]=1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:12]=[C:11]([C:17]3[CH:16]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:10]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 22136198HCID 22136198, compound

Product 1

HCID 10172758HCID 10172758, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Formula I where R1 is Pyridin-3-yl, R2 is Pyridin-2-yl, and R3 is 4-Fluorophenyl A mixture of 1 eq. (175 mg, 0.402 mmol) of 4-fluoro-N-[3-iodo-5-(pyridin-3-yloxy)-phenyl]-benzamide 1.15 eq. (170 mg, 0.463 mmol) of 2-tributyltinpyridine, and 0.04 eq. (11 mg, 0.10 mmol) of bis(triphenylphosphine)dichloropalladium in 2 mL of THF was irradiated for in a microwave for 10 minutes an 170° C. The reaction mixture was filtered and concentrated in vacuo. Purification by chromatography over silica with 50% EtOAC/Hexane to 75% EtOAc/Hexane as the gradient eluant afforded 30 mg of a solid (4-fluoro-N-[3-pyridin-2-yl-5-(pyridin-3-yloxy)-phenyl]-benzamide, (19% yield). Mpt 160–162° C. MS (M+1) 386.1.

Workup

  1. customwas irradiated for in a microwave for 10 minutes an 170° C
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customPurification by chromatography over silica with 50% EtOAC/Hexane to 75% EtOAc/Hexane as the gradient eluant

Sources & evidence

ORD record
ord-14ac127f63bf40a58cfd602f22c9f343
Source dataset
uspto-grants-2006_05
Patent number
US07053094B2

Reaction notes

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