Acrylonitrile → HCID 58765170, compound

HRID 860748Notes

Reaction equation

HRID 860748 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[Br:5][C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[CH:12][CH:11]=[C:10]([C:21]([O:23][CH3:24])=[O:22])[CH:9]=2>>[Br:5][C:6]1[N:7]([CH2:3][CH2:2][C:1]#[N:4])[C:8]2[C:13]([C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[CH:12][CH:11]=[C:10]([C:21]([O:23][CH3:24])=[O:22])[CH:9]=2

Participants

3

Reactant 2

HCID 7855AcrylonitrileHCID 11175076Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

Product 1

HCID 58765170HCID 58765170, compoundYield 74%

Conditions

Temperature
100 °C

Procedure

Acrylonitrile (10 mL of 1.52 M in 1,4-dioxane, 30.4 mmol) was added to methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (840 mg, 2.5 mmol) in a microwave vial. The vial was sealed and Triton® B (500 □L1.1□mol) was added via syringe. The vial was heated in a microwave apparatus for 1 hr at 100° C. The solution was cooled and poured to precipitate the crude product. The granular solid was collected, washed with water and dried. Recrystallization from ethanol gave the product as a colorless solid (696 mg, 74%). MS m/z 390 (MS+); 1H NMR (300 MHz, DMSO-D6) δ ppm 1.27–1.49 (m, 3 H) 1.60–2.01 (m, 7 H) 2.77–2.90 (m, 1 H) 2.98 (t, J=6.40 Hz, 2 H) 3.87 (s, 3 H) 4.62 (t, J=6.59 Hz, 2 H) 7.67 (dd, J=8.42, 1.46 Hz, 1 H) 7.83 (d, J=8.42 Hz, 1 H) 8.25 (s, 1 H).

Workup

  1. customThe vial was sealed
  2. additionTriton® B (500 □L1.1□mol) was added via syringe
  3. temperatureThe solution was cooled
  4. additionpoured
  5. customto precipitate the crude product
  6. customThe granular solid was collected
  7. washwashed with water
  8. customdried
  9. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-aa5b7b64f7f44a82b699f41cfd97b30a
Source dataset
uspto-grants-2006_12
Patent number
US07153848B2

Reaction notes

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