Acetone → HCID 22311917, compound

HRID 966540Notes

Reaction equation

HRID 966540 reaction equation
C([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:20])[CH:18]=2)[NH:13][C:12]=1[CH3:21])=[O:10])C1C=CC=CC=1.[C:22]([O-])([O-])=O.[K+].[K+].[CH3:28][C:29]([CH3:31])=[O:30]>>[CH3:21][C:12]1[NH:13][C:14]2[C:19]([C:11]=1[C:9]([OH:8])=[O:10])=[CH:18][C:17]([O:20][CH:28]([CH3:22])[C:29](=[O:30])[CH3:31])=[CH:16][CH:15]=2

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 109239755-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl ester

Product 1

HCID 22311917HCID 22311917, compoundYield 77%

Procedure

5-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl ester (1.0 g, 3.56 mmol), 2-bromobut-2-one (0.806 g, 5.33 mmol) and K2CO3 (1.47 g, 10.7 mmol) were mixed together in acetone (30 mL) and stirred at room temperature for 4 hours. The mixture was then filtered, concentrated under reduced pressure and redissolved in ethyl acetate. The resulting solution was washed with deionized water twice and dried over anhydrous Na2SO4. The crude was chromatographed (5% EtOAc/CH2Cl2) to give 0.97 g (77%) of 2-methyl-5-(1-methyl-2-oxo-propoxy)-1H-indole-3-carboxylic acid as a viscous oil. 1HNMR (400 MHz, DMSO): δ 1.36 (d, J=6.75 Hz, 3H), 2.06 (s, 3H, CH3CO), 2.59 (s, ArCH3), 4.67 (q, J=6.75 Hz, 1H), 5.28 (s, 2H), 6.73 (d, J=8.44 Hz, 1H), 7.23 (d, J=8.64 Hz, 1H), 7.29-7.46 (m, 6H), 11.76 (s, 1H, NH). MS (APCI+). Anal. Calcd for C21H21N1O4: C, 71.78; H, 6.02; N, 3.99. Found: C, 71.46: H, 6.04: N, 3.76. IR (KBr): 3276, 1715, 1659, 1458, 1168, 1078 cm−1.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated under reduced pressure
  3. dissolutionredissolved in ethyl acetate
  4. washThe resulting solution was washed with deionized water twice
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe crude was chromatographed (5% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-17db090ebb8247d982a7c02e75bc783e
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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