Potassium Iodide → 9-(2-hydroxy-2-methyl-3-phenoxypropyl)-9H-carbazole-3,6-dicarbonitrile

HRID 1752221Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][C:17]([CH3:27])([OH:26])[CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10](Br)=[CH:9][CH:8]=3.[C-:28]#[N:29].[Na+].[I-].[K+].[CH3:33][N:34](C)CCN>[Cu](I)I.C1(C)C=CC=CC=1>[OH:26][C:17]([CH3:27])([CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:16][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([C:33]#[N:34])=[CH:11][C:12]=2[C:13]2[C:5]1=[CH:4][CH:3]=[C:2]([C:28]#[N:29])[CH:14]=2

Participants

Conditions

Temperature: 100 °C

Procedure

An oven dried vial was charged with 1-(3,6-dibromo-9H-carbazol-9-yl)-2-methyl-3-phenoxypropan-2-ol (79.5 mg, 0.16 mmol), copper iodide (16 mg, 0.08 mmol), sodium cyanide (22 mg, 0.45 mmol) and potassium iodide (16 mg, 0.10 mmol). The sealed vial was nitrogen filled and evacuated three times before addition of N,N-dimethyl-1,2-ethanediamine (22.5 μl, 0.21 mmol) and anhydrous toluene (75 μl). The reaction was heated at 100° C. over 60 hours. The cooled mixture was diluted with EtOac, washed with water and brine. The organic layer was dried over Na2SO4, filtered and condensed. The crude mixture was purified on silica gel in 40% THF/hexanes. Yield=34%.

Workup

customAn oven dried vial
additionfilled
customevacuated three times
additionThe cooled mixture was diluted with EtOac
washwashed with water and brine
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customcondensed
customThe crude mixture was purified on silica gel in 40% THF/hexanes

Sources & evidence

ORD record: ord-3571cf1cd4e249d395eb68a9a26a7604
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09162980B2

Reaction notes

Loading…