Water → HCID 118271676, compound

HRID 590882Notes

Reaction equation

HRID 590882 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([NH:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:50][O:51][C:52]1[CH:57]=[CH:56][C:55]([CH2:58]Br)=[CH:54][CH:53]=1.O>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([N:30]([CH2:58][C:55]3[CH:56]=[CH:57][C:52]([O:51][CH3:50])=[CH:53][CH:54]=3)[CH2:31][C:32]3[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=3)=[N:9][N:10]([C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1650214-Methoxybenzyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 118272564HCID 118272564, compound

Product 1

HCID 118271676HCID 118271676, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., to a solution of 6-chloro-N-(4-methoxybenzyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine (2.0 g, 3.78 mmol) in anhydrous THF (30 mL) was added LiHMDS (1.0 M solution in Toluene, 7.56 mL, 7.56 mmol) and the contents were stirred at the same temperature. After 15 min, PMBBr (0.92 g, 4.53 mmol) was added at the same temperature and the contents were allowed to warm to ambient temperature. After 3 h, H2O (10 mL) was added and stirred for 5 min. The organic contents were extracted with EtOAc (3×40 mL) and the EtOAc layer washed with brine (1×20 mL), dried over anhydrous Na2SO4 and the solvents were removed under reduced pressure. The residue thus obtained was purified by a filter column to afford the title compound (1.0 g, 41% yield). MS ES calc'd. for C41H35ClN4O2 [M+H]+ 651. Found 651.

Workup

  1. waitAfter 3 h
  2. stirringstirred for 5 min
  3. extractionThe organic contents were extracted with EtOAc (3×40 mL)
  4. washthe EtOAc layer washed with brine (1×20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customthe solvents were removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by a filter column

Sources & evidence

ORD record
ord-96332c42dfc940d0b5c5c02e9825dd96
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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