Sodium Bicarbonate → HCID 21071400, compound

HRID 1371911Notes

Reaction equation

HRID 1371911 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:31]([Si:34](OS(C(F)(F)F)(=O)=O)([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36])([CH3:33])[CH3:32].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([Si:34]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[CH:31]([CH3:33])[CH3:32])[CH:13]=[C:12]2[CH2:18][CH2:19][N:20]1[C:21](=[O:30])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]1=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 1548084HCID 1548084, compoundHCID 2724529Triisopropylsilyl trifluoromethanesulfonate

Product 1

HCID 21071400HCID 21071400, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Combine a mixture of an oil dispersion of KH (40%, 1 g) in 30 mL anhydrous THF and a suspension of 2-(2-(5-benzyloxy-1H-indol-3-yl)ethyl)isoindole-1,3-dione (1.2 g, 3 mmol) in 30 mL THF portionwise. Stir for 1 hour at ambient temperature, cooled to 0° C., add triisopropylsilyltrifluoromethanesulfonate (1.85 g, 6 mmol) and stir an additional 1 hour at ambient temperature. Pour the reaction into a rapidly stirring solution of saturated NaHCO3 and extract with 2×50 mL EtOAc. Combine the organic layer, dry over MgSO4 and concentrate to dryness and chromatograph on silica gel eluting with 1% MeOH in CHCl3 to give 2-(2-(5-benzyloxy-1-triisopropylsilanyl-1H-indol-3-yl)ethyl)isoindole-1,3-dione as an oil.

Workup

  1. temperaturecooled to 0° C.
  2. stirringstir an additional 1 hour at ambient temperature
  3. additionPour
  4. extractionextract with 2×50 mL EtOAc
  5. dry with materialdry over MgSO4
  6. concentrationconcentrate to dryness and chromatograph on silica gel eluting with 1% MeOH in CHCl3

Sources & evidence

ORD record
ord-2320c925fd494eab9419c71a558c677f
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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