beta-Bromostyrene → 8-Chloro-2-methyl-5-styryl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1400560

Reaction equation

HRID 1400560 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.Br[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O>CN(C=O)C.[Cu]I>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH:17]=[CH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 7667beta-BromostyreneHCID 196158-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indoleHCID 62657Potassium Phosphate, TribasicHCID 145742L-Proline

Product 1

HCID 684813388-Chloro-2-methyl-5-styryl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

8-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (20 mg, 0.09 mmol), (2-Bromo-vinyl)-benzene (22 mg, 0.12 mmol), potassium phosphate (50 mg, 0.24 mmol), L-Proline (2 mg, 0.017 mmol), CuI (2 mg, 0.01 mmol) were stirred together in dry DMF (1 mL) at RT and N2 gas was purged into it for 5 min. The reaction mixture was heated in microwave at 100° C. for 5 h and then diluted with water. The desired compound was extracted with EtOAc, organic layer dried on anhydrous sodium sulfate, concentrated under vacuum to obtain crude compound which was purified by RHPLC to obtained 8-Chloro-2-methyl-5-styryl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as an off-white solid. Yield: 11 mg. 1H NMR (DMSO, TFA salt) δ (ppm): 7.90 (d, 1H), 7.80 (d, 1H), 7.65 (m, 3H), 7.42 (t, 2H), 7.30 (m, 2H), 6.98 (d, 1H), 4.60-4.30 (m, 2H), 4.0 (m, 1H), 3.70 (m, 1H), 3.25 (m, 2H), 3.02 (s, 3H).

Workup

  1. customN2 gas was purged into it for 5 min
  2. additiondiluted with water
  3. extractionThe desired compound was extracted with EtOAc, organic layer
  4. dry with materialdried on anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto obtain crude compound which
  7. customwas purified by RHPLC

Sources & evidence

ORD record
ord-c6e8ebfe851641e3b22bda1a2ec1afc1
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Linked notes

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