Hydrogen Peroxide → HCID 22638724, compound

HRID 1836621Notes

Reaction equation

HRID 1836621 reaction equation
C12BC(CCC1)CCC2.[C:10]1([CH3:35])[CH:15]=[CH:14][C:13]([S:16]([N:19]2[C:27]3[C:22](=[CH:23][C:24]([C:28]#[N:29])=[CH:25][CH:26]=3)[C:21]([CH:30]3[CH2:32][CH:31]3[CH:33]=[CH2:34])=[CH:20]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1.[OH-:36].[Na+].OO>C1COCC1.C(O)C>[OH:36][CH2:34][CH2:33][CH:31]1[CH2:32][CH:30]1[C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[C:24]([C:28]#[N:29])[CH:23]=2)[N:19]([S:16]([C:13]2[CH:12]=[CH:11][C:10]([CH3:35])=[CH:15][CH:14]=2)(=[O:18])=[O:17])[CH:20]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2×HCID 789669-Borabicyclo(3.3.1)nonaneHCID 22638753HCID 22638753, compound

Product 1

HCID 22638724HCID 22638724, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

9-Borabicyclo[3.3.1]nonane (4.1 ml of 0.5 M THF solution, 2.05 mmol) was added drop wise under a nitrogen atmosphere to a stirred solution of 1-(toluene-4-sulfonyl)-3-(2-vinyl-cyclopropyl)-1H-indole-5-carbonitrile (735 mg, 2.01 mmol) in dry THF (6 ml). The solution was heated to 30° C. for 6 hr and then cooled to 20° C. Absolute ethanol (12 ml), sodium hydroxide (2.6 ml of a 1N solution, 2.6 mmol), and hydrogen peroxide (0.85 ml of a 30% solution) were added sequentially to the stirred solution. The mixture was heated to 40° C. for 1 hr and then cooled to room temperature. Sodium hydroxide (2 ml of a 1N solution) was added and the mixture was extracted with ethyl acetate. The ethyl acetate extract was dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel using 3% acetone in methylene chloride as the eluent to give 3-[2-(2-hydroxy-ethyl)-cyclopropyl]-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile (300 mg, 45%). 1H NMR (300 MHz, CDCl3): δ8.01 (d, 2H), 7.97 (s, 1H), 7.73 (d, 1H), 7.28 (s, 1H), 7.24 (d, 2H), 3.80 (m, 2H), 2.35 (s, 3H), 1.74-1.62 (m, 4H), 1.08 (m, 1H), 0.90 (m, 1H), 0.83 (m, 1H). MS m/e 381.17 (MH+).

Workup

  1. temperaturecooled to 20° C
  2. temperatureThe mixture was heated to 40° C. for 1 hr
  3. temperaturecooled to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. dry with materialwas dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel using 3% acetone in methylene chloride as the eluent

Sources & evidence

ORD record
ord-8f3234e9b5184b19af8f2d2fbd1536e7
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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