Trityl chloride → 6-Chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 590768Notes

Reaction equation

HRID 590768 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([I:11])=[N:9][NH:10][C:4]=2[CH:3]=1.[H-].[Na+].[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([I:11])=[N:9][N:10]([C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 1784778336-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 895258586-Chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine (1.874 g, 6.71 mmol) in THF (20 mL) was treated with NaH (60% in mineral oil; 0.402 g, 10.06 mmol) at 0° C. and the mixture was stirred for 50 min. Trityl chloride (2.244 g, 8.05 mmol) was added at 0° C. and the mixture was stirred for 16 h at room temperature, quenched with saturated NH4Cl, and extracted with EtOAc. The organic phase was washed with water, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified via flash chromatography (0-10% EtOAc-hexanes) to yield 6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine. MS ESI calc'd. for C25H18ClIN3[M+1]+ 522. found 522.

Workup

  1. stirringthe mixture was stirred for 16 h at room temperature
  2. customquenched with saturated NH4Cl
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via flash chromatography (0-10% EtOAc-hexanes)

Sources & evidence

ORD record
ord-965d577c8faa4636a89d6f1b5642d514
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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