Hydrochloric Acid → HCID 66750308, compound

HRID 1788004Notes

Reaction equation

HRID 1788004 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21].[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].N12CCCN=C1CCCCC2.Cl>ClCCl>[C:25]([Si:22]([CH3:24])([CH3:23])[O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 28928tert-Butyldimethylsilyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57437985HCID 57437985, compound

Product 1

HCID 66750308HCID 66750308, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 32.26 g (0.115 mol) of 2-(5-hydroxy-1H-indazol-3-yl)-1H-isoindole-1,3(2H)-dione in 320 ml of dichloromethane, a solution of 43.54 g (0.288 mol) of TBDMS chloride in 150 ml of dichloromethane was added. The resulting mixture was treated dropwise with 35.5 ml (0.23 mol) of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) at room temperature, obtaining a clear solution. After 3 hours the reaction mixture was poured in 300 ml of a solution 0.1 N of hydrochloric acid. The aqueous layer was separated and extracted with 200 ml of dichloromethane. Organic extracts were dried over sodium sulfate and the solvent evaporated under vacuum. The raw product was purified by flash chromatography over silica gel eluiting with dichloromethane-cyclohexane-ethyl acetate (4:4:2). 36.03 g of product as white solid were obtained. Yield=79.2%. mp=225-228° C. HPLC r.t. 8.3 [M+H]+=394 [2M+H]+=787

Workup

  1. customobtaining a clear solution
  2. customThe aqueous layer was separated
  3. extractionextracted with 200 ml of dichloromethane
  4. dry with materialOrganic extracts were dried over sodium sulfate
  5. customthe solvent evaporated under vacuum
  6. customThe raw product was purified by flash chromatography over silica gel eluiting with dichloromethane-cyclohexane-ethyl acetate (4:4:2)

Sources & evidence

ORD record
ord-39d7897e17fc4837875fe505c7715078
Source dataset
uspto-grants-2009_03
Patent number
US07511136B2

Reaction notes

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