Toluene → HCID 10043341, compound

HRID 902037Notes

Reaction equation

HRID 902037 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:16]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[C:27]1(C)C=CC=C[CH:28]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:27]([C:2]1[N:7]=[C:6]([C:8]2[C:16]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:4][CH:3]=1)=[CH2:28]

Participants

4

Reactant 2

HCID 1140TolueneHCID 59700605HCID 59700605, compound

Product 1

HCID 10043341HCID 10043341, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

Add tributylvinylstanane (0.056 mL, 0.182 mmol) to a solution of 4-[2-(6-chloro-pyridin-2-yl)-pyrazolo[1,5-a]pyridin-3-yl]-quinoline (59 mg, 0.165 mmol) in toluene (0.83 mL) at room temperature and bubble nitrogen through the solution for 5 minutes. Add tetrakis(triphenylphosphine) palladium (0) (9 mg, 0.008 mmol) and bubble nitrogen through the solution for 1 minute. Heat the reaction to 110° C. for 15 hours. Purify by flash column chromatography (Silica Gel, 20-40% acetone/hexanes) to provide the title compound 11.5 mg (20%) as a white solid.

Workup

  1. custombubble nitrogen through the solution for 5 minutes
  2. temperatureHeat
  3. customthe reaction to 110° C. for 15 hours
  4. customPurify by flash column chromatography (Silica Gel, 20-40% acetone/hexanes)

Sources & evidence

ORD record
ord-b04fc36602044a15836b33ec3c9e0b9a
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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