Pentane → 2-({9-[(5-Chloro-1-benzothiophen-3-yl)methyl]-9H-carbazol-4-yl}oxy)acetonitrile

HRID 1057644Notes

Reaction equation

HRID 1057644 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([O:14][CH2:15][C:16]#[N:17])=[CH:3][CH:2]=1.CCCCC.[H-].[Na+].Br[CH2:26][C:27]1[C:31]2[CH:32]=[C:33]([Cl:36])[CH:34]=[CH:35][C:30]=2[S:29][CH:28]=1>CN(C=O)C>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]2[S:29][CH:28]=[C:27]([CH2:26][N:12]3[C:13]4[CH:1]=[CH:2][CH:3]=[C:4]([O:14][CH2:15][C:16]#[N:17])[C:5]=4[C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:31]=2[CH:32]=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 27798573-(Bromomethyl)-5-chloro-1-benzothiopheneHCID 18671668(9H-Carbazol-4-yloxy)acetonitrile

Product 1

HCID 186716802-({9-[(5-Chloro-1-benzothiophen-3-yl)methyl]-9H-carbazol-4-yl}oxy)acetonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(9H-Carbazol-4-yloxy)acetonitrile (0.146 g, 0.66 mmol)) is added to a slurry of pentane-washed NaH (0.0441 g, 0.0011 mol) in DMF (1 mL) and allowed to stir for 20 min at room temperature. 3-(Bromomethyl)-5-chlorobenzothiophene (0.229 g, 0.88 mmol) is added and after stirring for 1 h the mixture is partitioned between ethyl acetate and water. The combined organic layers are dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (75 mL) using ethyl acetate/hexane (20/80) and solids are precipitated using dichloromethane/hexane to give 0.148 g (56%) of the title compound; MS (ESI+) for C23H15ClN2OS m/z 425.2 (M+Na); IR (drift) 1581, 1460, 1439, 1332, 1279, 1232, 1221, 1155, 1148, 1115, 1079, 833, 780, 752, 717 cm−1; 1H NMR (CDCl3) δ5.10, 5.70, 6.72, 6.80, 7.12, 7.28-7.47, 7.80, 7.87, 8.36. Anal. Calcd for C23H15ClN2OS: C, 68.57; H, 3.75; N, 6.95. Found: C, 68.87; H, 4.22; N, 6.56.

Workup

  1. stirringafter stirring for 1 h the mixture
  2. customis partitioned between ethyl acetate and water
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. concentrationconcentrated to an oil
  5. customThe oil is chromatographed on silica gel (75 mL)
  6. customare precipitated

Sources & evidence

ORD record
ord-7666177effb844e4b4cf9e1ff35fb083
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

Loading…