Trityl chloride → 3-(4-Bromothiazol-2-yl)-1-trityl-pyrazolo[5,4-b]pyridine

HRID 1044027Notes

Reaction equation

HRID 1044027 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][N:8]=2)[S:5][CH:6]=1.[H-].[Na+].Cl[C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:8]=2)[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 178419473HCID 178419473, compound

Product 1

HCID 681079193-(4-Bromothiazol-2-yl)-1-trityl-pyrazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-bromothiazol-2-yl)-1H-pyrazolo[5,4-b]pyridine (161 mg, 0.5727 mmol) in DMF (3 mL) was cooled to 0° C. then sodium hydride (27.49 mg, 0.6872 mmol) was added in one portion. Stirred at 0° C. for 30 mins before (chloro-diphenyl-methyl)benzene (167.6 mg, 0.6013 mmol) was added. Ice-bath removed and stirred at room temperature for 2 h. Quenched with water, diluted with EtOAc. Organic layer then collected, washed with brine, dried (MgSO4), filtered and concentrated in vacuo.

Workup

  1. additionwas added
  2. customIce-bath removed
  3. customQuenched with water
  4. additiondiluted with EtOAc
  5. customOrganic layer then collected
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb4000145e464270b80dd48d9fe43aab
Source dataset
uspto-grants-2013_10
Patent number
US08563576B2

Reaction notes

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