Imidazole → HCID 68949735, compound

HRID 2116725Notes

Reaction equation

HRID 2116725 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([OH:13])=[O:12])[NH:8]2)=[CH:4][CH:3]=1.N1C=CN=C1.[CH3:19][C:20]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C1COCC1>[C:20]([Si:23]([CH3:25])([CH3:24])[O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([OH:13])=[O:12])[NH:8]2)=[CH:4][CH:3]=1)([CH3:22])([CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 223501916-Hydroxy-1H-indole-2-carboxylic acid

Product 1

HCID 68949735HCID 68949735, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Hydroxy-1H-indole-2-carboxylic acid (5.40 g, 30.48 mmol) is dissolved in THF (100 ml) and imidazole (10.38, 152.4 mmol) is added. The mixture is stirred for 5 minutes, TBDMS-Cl (13.78 g, 91.44 mmol) is added. The reaction is stirred at room temperature for 1 hour. The mixture is filtered into water (200 ml). The solid is washed with THF (50 ml). The filtrate is concentrated to remove THF. The product is extracted with ethyl acetate (100 ml) three times. The organic is dried (MgSO4), filtered, and concentrated to provide 6-(tert-Butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid (8.0 g, 90% yield). 1H NMR (400 MHz, DMSO-d6): δ 12.73 (s, 1H) , 11.43 (s, 1H), 7.49 (d, 1H), 7.00 (s, 1H), 6.84 (s, 1H), 6.63 (m, 1H), 0.97 (s, 9H), 0.20 (s, 6H).

Workup

  1. stirringThe reaction is stirred at room temperature for 1 hour
  2. filtrationThe mixture is filtered into water (200 ml)
  3. washThe solid is washed with THF (50 ml)
  4. concentrationThe filtrate is concentrated
  5. customto remove THF
  6. extractionThe product is extracted with ethyl acetate (100 ml) three times
  7. dry with materialThe organic is dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-00cb47dc47c048ecbd80264e0849eb3e
Source dataset
uspto-grants-2008_10
Patent number
US07439249B2

Reaction notes

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