2-Bromopropane → 3-Ethoxycarbonyl-9-isopropyl-9H-pyrido[3,4-b]indole

HRID 2217752Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:11]([O:13][C:14]([C:16]1[N:28]=[CH:27][C:19]2[NH:20][C:21]3[C:26]([C:18]=2[CH:17]=1)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:15])[CH3:12].Br[CH:30]([CH3:32])[CH3:31]>C1COCC1>[CH2:11]([O:13][C:14]([C:16]1[N:28]=[CH:27][C:19]2[N:20]([CH:30]([CH3:32])[CH3:31])[C:21]3[C:26]([C:18]=2[CH:17]=1)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:15])[CH3:12]

Participants

Conditions

Temperature: 60 °C

Procedure

Potassium bis-(trimethylsilyl)amide (5.48 g, 27.5 mmol) was added portionwise over 5 minutes under an atmosphere of argon to a stirred solution of 3-ethoxycarbonyl-9H-pyrido[3,4-b]indole (6 g, 25 mmol) in THF (60 ml) at 0° C. After 1 hour, 2-bromopropane (19 ml, 0.2 mol) was added dropwise over 10 minutes at room temperature and the reaction mixture was then heated to 60° C. for 18 hours. The mixture was concentrated in vacuo and the residue was dissolved in EtOAc. The solution was washed with water and then brine. The organic phase was separated, dried, filtered and concentrated in vacuo. The crude product was purified by flash eluting over a gradient of 0-70% EtOAc in isohexane. The product was obtained as a yellow solid (2.91 g) after evaporation of the appropriate fractions. NMR (300 MHz) 9.21 (s, 1H), 8.92 (s, 1H), 8.41 (d, 1H), 7.86 (d, 1H), 7.62 (t, 1H), 7.33 (t, 1H), 5.28 (m, 1H), 4.37 (q, 2H), 1.69 (d, 6H), 1.37 (t, 3H); m/z 283.5.

Workup

concentrationThe mixture was concentrated in vacuo
dissolutionthe residue was dissolved in EtOAc
washThe solution was washed with water
customThe organic phase was separated
customdried
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by flash
washeluting over a gradient of 0-70% EtOAc in isohexane

Sources & evidence

ORD record: ord-908e816f8d7c4da0a1a9919c58d05d79
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408064B2

Reaction notes

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