Sodium Hydroxide → HCID 59513826, compound

HRID 1159946Notes

Reaction equation

HRID 1159946 reaction equation
[CH3:1][C:2]([Si:5]([CH3:37])([CH3:36])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]2[N:14]=[C:15]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-:35])=[O:34])[CH:28]=3)[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19](S(C)(=O)=O)[N:18]=3)=[C:10]2[CH:9]=1)([CH3:4])[CH3:3].[BH4-].[Na+].[OH-].[Na+]>C(Cl)Cl.C(O)C>[CH3:4][C:2]([Si:5]([CH3:37])([CH3:36])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]2[N:14]=[C:15]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-:35])=[O:34])[CH:28]=3)[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][N:18]=3)=[C:10]2[CH:9]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 59513737HCID 59513737, compound

Product 1

HCID 59513826HCID 59513826, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-3-[2-(methylsulfonyl)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine (3.00 g, 5.56 mmol) in DCM (90 mL) and ethanol (90 mL), NaBH4 (526 mg, 13.9 mmol) was added one portion at rt. The mixture was stirred at rt for 1 h. The reaction mixture was poured into aq. 1N NaOH and extracted with DCM. The organic layer was combined, washed with brine and dried (Na2SO4). The solvent was evaporated under reduced pressure. Chromatography on silica gel eluting with DCM/EtOAc gradient (0-20% EtOAc) gave a pale yellow solid (1.87 g).

Workup

  1. extractionextracted with DCM
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-828127f7e1d540a7808c590d4412152e
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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