Trityl chloride → (R)-tert-butyl 3-(3-(3-bromo-1-trityl-1H-indazol-5-yl)-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate

HRID 1465699Notes

Reaction equation

HRID 1465699 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]3[N:17]=[C:16]([C@@H:18]4[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]4)[NH:15][N:14]=3)[CH:11]=2)[NH:6][N:5]=1.[C:31](Cl)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]3[N:17]=[C:16]([C@@H:18]4[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]4)[NH:15][N:14]=3)[CH:11]=2)[N:6]([C:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:5]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 178451955HCID 178451955, compound

Product 1

HCID 86695578(R)-tert-butyl 3-(3-(3-bromo-1-trityl-1H-indazol-5-yl)-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Added Sodium Hydride (100 mg; 2.5 mmol) to a solution of (R)-tert-butyl 3-(3-(3-bromo-1H-indazol-5-yl)-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate (530 mg, 0.988 mmol) in DMF (5 ml) at 0° C., then stirred for 30 minutes. Trityl Chloride (570 mg, 2.05 mmol) was added, and stirred at room temperature overnight. Added water (100 ml), filtered precipitated solid, washed with water, dried, then chromatographed on silica gel eluting with 30% v/v EtOAc/Hexanes to yield a mixture of mono and dialkylated products (560 mg, 8:2 mono/dialkylation).

Workup

  1. stirringstirred at room temperature overnight
  2. filtrationAdded water (100 ml), filtered
  3. customprecipitated solid
  4. washwashed with water
  5. customdried
  6. customchromatographed on silica gel eluting with 30% v/v EtOAc/Hexanes
  7. customto yield
  8. additiona mixture of mono and

Sources & evidence

ORD record
ord-2a0424c0ea7443a197beef34032ad632
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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