Water → HCID 21868730, compound

HRID 857463Notes

Reaction equation

HRID 857463 reaction equation
[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:19][C:20]#[N:21].O>CN(C=O)C>[C:20]([CH2:19][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([I:1])[CH:10]=2)[CH:6]=[C:7]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:21]

Participants

6

Reactant 4

HCID 962WaterHCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 21868755HCID 21868755, compound

Product 1

HCID 21868730HCID 21868730, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 6-iodoindole-2-carboxylate (7.0 g, 22 mmol) in DMF (25 mL) was added dropwise over 15 min to a stirred suspension of sodium hydride (60%, 1.36 g, 34 mmol) in DMF (50 mL) at 0° C. under Ar. The reaction was stirred at 0° C. for 45 min then chloroacetonitrile (2.85 mL, 45 mmol) was added in one portion. The reaction was then heated to 75° C. and stirred for one h. After allowing to cool to room temperature the mixture was poured into water (300 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with brine (1×200 ml), dried (magnesium sulfate), filtered and the solvent removed under vacuum to give the product (1.8 g, 23%). IR νmax (Nujol)/cm−1 2924, 2854, 1895, 1703, 1601, 1527, 1464, 1446, 1426, 1398, 1377, 1366, 1334, 1308, 1261, 1204, 1148, 1135, 1119, 1103, 1048, 1024, 989, 949, 904, 894, 871, 842, 833, 800, 786, 762, 736, 654, 612, 584 and 471; NMR δH (400 MHz; CDCl3) 7.79 (1H, s), 7.51 (1H, d, J 8.6 Hz), 7.42 (1H, d, J 8.6 Hz), 7.32 (1H, s), 5.54 (2H, s), 4.37 (2H, q, J 7 Hz), 1.39 (3H, t, J 7 Hz).

Workup

  1. temperatureThe reaction was then heated to 75° C.
  2. stirringstirred for one h
  3. temperatureto cool to room temperature the mixture
  4. extractionextracted with ethyl acetate (3×200 mL)
  5. washThe combined organic extracts were washed with brine (1×200 ml)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-03e0d8f986804afb8ee584a6818e65e2
Source dataset
uspto-grants-2006_12
Patent number
US07145009B2

Reaction notes

Loading…