Tetrabutylammonium Fluoride → 3-amino-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole

HRID 2217756Notes

Reaction equation

HRID 2217756 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C[Si](C)(C)CCOC([NH:26][C:27]1[N:42]=[CH:41][C:30]2[N:31]([CH:38]([CH3:40])[CH3:39])[C:32]3[C:37]([C:29]=2[C:28]=1[CH2:43][CH3:44])=[CH:36][CH:35]=[CH:34][CH:33]=3)=O>>[NH2:26][C:27]1[N:42]=[CH:41][C:30]2[N:31]([CH:38]([CH3:40])[CH3:39])[C:32]3[C:37]([C:29]=2[C:28]=1[CH2:43][CH3:44])=[CH:36][CH:35]=[CH:34][CH:33]=3

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 693078183-[2-(Trimethylsilyl)ethoxycarbonylamino]-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole

Product 1

HCID 693095793-amino-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indoleYield 67.1%

Conditions

Temperature
50 °C

Procedure

Tetrabutylammonium flouride (1M in THF, 5 ml, 5 mmol) was added to 3-[2-(trimethylsilyl)ethoxycarbonylamino]-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole (Method 4; 80 mg, 0.2 mmol) and the mixture was heated to 50° C. for 1 hour. The mixture was concentrated in vacuo and the residue was dissolved in DCM and washed with water. The organic phase was separated, dried and evaporated in vacuo. The crude product was purified by flash eluting over a gradient of 0-2.5% MeOH in DCM. The product was obtained as a light brown solid (34 mg) after evaporation of the appropriate fractions. NMR (300 MHz, CDCl3) 8.40 (s, 1H), 8.16 (d, 1H), 7.48 (m, 2H), 7.18 (t, 1H), 4.91 (m, 1H), 3.13 (q, 2H), 1.69 (d, 6H), 1.40 (t, 3H); m/z 255.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water
  4. customThe organic phase was separated
  5. customdried
  6. customevaporated in vacuo
  7. customThe crude product was purified by flash
  8. washeluting over a gradient of 0-2.5% MeOH in DCM

Sources & evidence

ORD record
ord-2c46f3ef29d1438dac04445e73b72dbd
Source dataset
uspto-grants-2008_08
Patent number
US07408064B2

Reaction notes

Loading…