Water → HCID 59170301, compound

HRID 1445905Notes

Reaction equation

HRID 1445905 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].[Na+].[I-].[CH2:9]([N:16]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:25])[C:19]=2[CH:18]=[C:17]1[CH3:26])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O.CN([CH:31]=[O:32])C>>[CH3:1][O:4][C:31](=[O:32])[CH:12]([O:25][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:19]=1[CH:18]=[C:17]([CH3:26])[N:16]2[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:11][CH:10]([CH3:15])[CH3:9]

Participants

6

Reactant 5

HCID 962WaterHCID 5238Sodium IodideHCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 107523601-Benzyl-2-methyl-1H-indol-4-ol

Product 1

HCID 59170301HCID 59170301, compound

Conditions

Temperature
70 °C

Procedure

To a stirred suspension of K2CO3 (0.563 g, 4.22 mmol), NaI (0.031 g, 0.21 mmol) and 1-benzyl-2-methyl-1H-indol-4-ol (1) (0.500 g, 2.11 mmol) in dry DMF (15 mL), a solution of (CH3)2CHCH2BrCHCO2Me (0.66 g, 3.2 mmol) in DMF (5 mL) was added dropwise. The reaction mixture was heated at 70° C. for 7 h, cooled to room temperature and water (30 mL) was added. The mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), dried over Na2SO4 and evaporated. Flash chromatography of the residue over silica gel, using 10% EtOAc in hexanes to 20% EtOAc in hexanes, gave product 2 as a pale yellow solid. Yield: 0.54 g (70%).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with EtOAc (3×50 mL)
  3. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-bda16d9f9a3d421395c07d502830add2
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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