Dichloromethane → 7-Bromo-4-(4-chloro-2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

HRID 8262

Reaction equation

HRID 8262 reaction equation
S(Cl)(Cl)(=O)=O.Cl[CH2:7][Cl:8].[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([C:20]3[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)=[N:23][N:22]4[CH2:31][CH2:32]C[C:21]=34)=[CH:15][CH:16]=[N:17]2)=[CH:12][CH:11]=1>N1C=CC=CC=1>[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([C:20]3[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)=[N:23][N:22]4[CH2:31][CH2:32][CH:7]([Cl:8])[C:21]=34)=[CH:15][CH:16]=[N:17]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24648Sulfuryl chlorideHCID 219925197-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

Product 1

HCID 101132117-Bromo-4-(4-chloro-2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1 M sulfuryl chloride in dichloromethane (20 mL, 20 mmol) is added to a solution of 7-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (2.2 g, 5.62 mmol) in dry pyridine (50 mL). The mixture is stirred for 18 h and concentrated in vacuo. The residue is partitioned between chloroform and saturated sodium chloride. The organic layer is dried (sodium sulfate), filtered, concentrated in vacuo, and the residue chromatographed on SiO2 (dichloromethane to 20% methanol in dichloromethane) to yield the title compound as a red solid, 1.8 g (75%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is partitioned between chloroform and saturated sodium chloride
  3. dry with materialThe organic layer is dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customthe residue chromatographed on SiO2 (dichloromethane to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5117de9338de4a369384dbd7fc1bb107
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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