4-(2-(6-Chloropyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline → 4-[2-(6-Vinyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline

HRID 8283

Reaction equation

HRID 8283 reaction equation
[CH2:1](C([Sn])=C(CCCC)CCCC)[CH2:2]CC.Cl[C:17]1[N:22]=[C:21]([C:23]2[C:24]([C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:34]=[CH:33][CH:32]=3)=[C:25]3[CH2:30][CH2:29][CH2:28][N:26]3[N:27]=2)[CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=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:1]([C:17]1[N:22]=[C:21]([C:23]2[C:24]([C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:34]=[CH:33][CH:32]=3)=[C:25]3[CH2:30][CH2:29][CH2:28][N:26]3[N:27]=2)[CH:20]=[CH:19][CH:18]=1)=[CH2:2]

Participants

5

Reactant 2

HCID 219927874-(2-(6-Chloropyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolineHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 102687504-[2-(6-Vinyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolineYield 62%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Add tributylvinyltin (0.059 mL, 0.19 mmol) to a solution of 4-[2-(6-chloro-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline, EXAMPLE 101, (59 mg, 0.17 mmol) in toluene (0.7 mL) at RT. Bubble nitrogen into the reaction mixture for 5 min and add tetrakis-(triphenylphosphine) palladium (0) (10 mg, 0.0085 mmol). Bubble nitrogen into the solution for an additional 2 min and heat the reaction to 110° C. for 18 h. Concentrate the reaction in vacuo and purify by flash column chromatography (SiO2, 20-40% acetone/hexanes) to provide the title compound (35 mg, 62%) as a white solid.

Workup

  1. waitBubble nitrogen into the solution for an additional 2 min
  2. temperatureheat
  3. customthe reaction to 110° C. for 18 h
  4. concentrationConcentrate
  5. customthe reaction in vacuo
  6. custompurify by flash column chromatography (SiO2, 20-40% acetone/hexanes)

Sources & evidence

ORD record
ord-b77d1639029d4675ac57aa188f0309f6
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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