tert-Butyldimethylsilyl chloride → HCID 66750061, compound

HRID 1788001Notes

Reaction equation

HRID 1788001 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[C:19](=[O:20])[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]3=[O:21])=[N:7][NH:8]2)=[CH:4][CH:3]=1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].N12CCCN=C1CCCCC2>ClCCl.Cl>[Si:22]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[C:19](=[O:20])[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]3=[O:21])=[N:7][NH:8]2)=[CH:4][CH:3]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 136082911HCID 136082911, compound

Product 1

HCID 66750061HCID 66750061, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of 15.03 g (53.82 mmol) of 2-({6-hydroxy}-1H-indazol-3-yl)-1H-isoindole-1,3(2H)-dione in 150 ml of dichloromethane, a solution of 20.19 g (0.134 mol) of TBDMS chloride in 75 ml of dichloromethane was added. The resulting mixture was treated dropwise with 12.06 ml (80.73 mmol) 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 250 ml of 0.5 N HCl. The aqueous layer was separated and extracted with 120 ml of dichloromethane. Organic extracts were dried over sodium sulfate and the solvent evaporated under vacuum. The moist raw product was stirred in 50 ml of ethyl acetate at 50° C. Then, about one half of the solvent was evaporated under vacuum and the mixture was treated dropwise with 100 ml of cyclohexane. The product was isolated by suction as light yellow solid (15.04 g). Yield=71.0%. mp=207-209° C.

Workup

  1. customobtaining a clear solution
  2. customThe aqueous layer was separated
  3. extractionextracted with 120 ml of dichloromethane
  4. dry with materialOrganic extracts were dried over sodium sulfate
  5. customthe solvent evaporated under vacuum
  6. customThen, about one half of the solvent was evaporated under vacuum
  7. additionthe mixture was treated dropwise with 100 ml of cyclohexane

Sources & evidence

ORD record
ord-5dcdf5a0b0944f23af127e9d4e22bfa2
Source dataset
uspto-grants-2009_03
Patent number
US07511136B2

Reaction notes

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