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

HRID 8254Notes

Reaction equation

HRID 8254 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:11]1[N:16]=[C:15]([C:17]2[C:18]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=[CH:27][CH:26]=3)=[C:19]3[CH2:24][CH2:23][CH2:22][N:20]3[N:21]=2)[CH:14]=[CH:13][CH:12]=1>O1CCCC1.[Cl-].[Zn+2].[Cl-].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>[CH2:1]([C:11]1[N:16]=[C:15]([C:17]2[C:18]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=[CH:27][CH:26]=3)=[C:19]3[CH2:24][CH2:23][CH2:22][N:20]3[N:21]=2)[CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 102004464-(2-(6-Bromopyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolineHCID 178418336HCID 178418336, compound

Product 1

HCID 102724674-[2-(6-Benzyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Zinc(II) chloride (0.34 mL, 1.0 M solution, 0.34 mmol) is added, at room temperature with stirring, to a solution of benzyl magnesium chloride (0.15 mL, 2.0 M solution, 0.31 mmol) in tetrahydrofuran (1 mL). After 15 min, Pd(PPh3)2Cl2 (5.4 mg, 0.0076 mmol) is added followed by a solution of 4-[2-(6-bromo-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline (60 mg 0.153 mmol) in tetrahydrofuran (1 mL). The reaction mixture is stirred for 18 h at room temperature and quenched with saturated aqueous ammonium chloride (1 mL). The reaction mixture is concentrated in vacuo, filtered, and the residue chromatographed on SiO2 (20-50% acetone/hexanes) to yield the title compound, 33.4 mg (54%), as a white solid.

Workup

  1. customquenched with saturated aqueous ammonium chloride (1 mL)
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. filtrationfiltered
  4. customthe residue chromatographed on SiO2 (20-50% acetone/hexanes)

Sources & evidence

ORD record
ord-12f27f75f99d47e4a40c92fcb9b23588
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

Loading…