Carbazole → HCID 58516589, compound

HRID 1913849Notes

Reaction equation

HRID 1913849 reaction equation
I[C:2]1[CH:7]=[C:6]([C:8]([CH3:15])([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:9])[CH:5]=[CH:4][C:3]=1[O:16][CH2:17][O:18][CH3:19].[CH:20]1[C:32]2[NH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]=2[CH:23]=[CH:22][CH:21]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN(C)[C@@H]1CCCC[C@H]1N>[Cu]I.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:19][O:18][CH2:17][O:16][C:3]1[CH:4]=[CH:5][C:6]([C:8]([CH3:15])([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:9])=[CH:7][C:2]=1[N:31]1[C:32]2[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=2[C:25]2[C:30]1=[CH:29][CH:28]=[CH:27][CH:26]=2

Participants

8

Reactant 4

HCID 6854CarbazoleHCID 62657Potassium Phosphate, TribasicHCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamineHCID 58516558HCID 58516558, compound

Product 1

HCID 58516589HCID 58516589, compoundYield 31.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 30 mL of dry toluene add 2-iodo-1-(methoxymethoxy)-4-(2,4,4-trimethylpentan-2-yl)benzene (1.50 g, 3.986 mmol), carbazole (0.633 g, 3.786 mmol), K3PO4 (1.71 g, 8.034 mmol), CuI (0.158 g, 0.830 mmol) and trans-N,N-dimethylcyclohexane-1,2-diamine (0.158 g, 1.111 mmol). Reflux the reaction mixture for 48 hours, cool, filter, and concentrate to give material. Purify material by flash chromatography using 3% ethyl acetate in hexanes to give 0.49 g (29.6%) of 9-(2-(methoxymethoxy)-5-(2,4,4-trimethylpentan-2-yl)phenyl)-9H-carbazole as off-white powder. 1H NMR (400 MHz, CDCl3) δ 8.19-8.14 (m, 2H), 7.50-7.25 (m, 7H), 7.19-7.13 (m, 2H), 4.93 (s, 2H), 3.16 (s, 3H), 1.76 (s, 2H), 1.40 (s, 6H), 0.82 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 151.41 (s), 144.96 (s), 141.46 (s), 127.95 (s), 127.19 (s), 126.13 (s), 125.68 (s), 123.11 (s), 120.13 (s), 119.39 (s), 116.20 (s), 110.05 (s), 94.99 (s), 56.99 (s), 56.06 (s), 38.27 (s), 32.40 (s), 31.85 (s), 31.58 (s);

Workup

  1. temperatureReflux the reaction mixture for 48 hours
  2. temperaturecool
  3. filtrationfilter
  4. concentrationconcentrate
  5. customto give material

Sources & evidence

ORD record
ord-d5e384d0bf674ee887e49ed63043d17e
Source dataset
uspto-grants-2013_12
Patent number
US08609794B2

Reaction notes

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