Water → HCID 68735775, compound

HRID 2278477Notes

Reaction equation

HRID 2278477 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([I:15])=[CH:9][CH:8]=3.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[I:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([I:1])=[CH:3][CH:4]=3

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 7416311-Bromo-1-undecanolHCID 31164883,6-Diiodo-9H-carbazole

Product 1

HCID 68735775HCID 68735775, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,6-diiodocarbazole (10.0 g, 23.87 mmol) and 11-bromo-1-undecanol (7.0 g, 27.87 mmol) in DMF (100.0 ml) was added K2CO3 (32.0 g, 231.33 mmol). The reaction was carried out at room temperature for 24 h. Water (300 ml) was added. The precipitate was filtered. The crude product was purified by silica gel column using Hexane/ethyl acetate (7:3) as solvent. 12.4 g (87.9%) of pure product as white solid was obtained. 1H-NMR (CDCl3, TMS, 500 MHZ): δ=8.32 (d, 2Harom, J=1.5 Hz), 7.71 (dd, 2Harom, J1=1.5 Hz, J2=8.5 Hz), 7.16 (dd, 2Harom, J1=1.5 Hz, J2=8.5 Hz), 4.21 (t, 2H, NCH2), 3.64 (m, 2H, OCH2), 3.41 (t, 1H, OH), 1.81 (m, 4H, 2×CH2), 1.54 (m, 4H, 2×CH2), 1.30 (m, 10H, 5×CH2) ppm.

Workup

  1. filtrationThe precipitate was filtered
  2. customThe crude product was purified by silica gel column

Sources & evidence

ORD record
ord-01f4d9665eca4e77b9004544e806c790
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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