Sodium hydride → HCID 136342114, compound

HRID 748522Notes

Reaction equation

HRID 748522 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2)#[N:2].[H-].[Na+].[CH2:15]([O:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][C:22](Cl)=[N:21][CH:20]=1)[CH3:16].[NH4+].[Cl-]>CN(C)C=O.O>[OH:12][C:7]1[NH:8][C:9]2[C:5]([C:6]=1[C:22]1[CH:23]=[CH:24][C:19]([C:18]([O:17][CH2:15][CH3:16])=[O:26])=[CH:20][N:21]=1)=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrileHCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 136342114HCID 136342114, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
110 °C

Procedure

To a solution of 5-cyanooxindole (360 mg, 2.27 mmol) in N,N-dimethylformamide (5 mL) was added sodium hydride (106 mg, 4.41 mmol). The greenish reaction mixture was stirred for 50 min whereafter 6-chloronicotinic acid ethyl ester (350 mg, 1.89 mmol) dissolved in N,N-dimethylformamide (5 mL) was added. The reaction mixture was heated at 110° C. for 30 min and water (50 mL) and saturated NH4Cl(aq) (20 mL) was added, followed by extraction with ethyl acetate. The phases were separated and the organic phase contained the title compound as a precipitation that was filtered off. The solvent was concentrated in vacuo and additional product precipitated that was filtered to give 200 mg (34% yield) of the title compound in total: 1H NMR (DMSO-d6, 300 MHz) δ 14.50 (br s, 1 H), 11.00 (s, 1 H), 8.73 (s, 1 H), 7.95 (s, 2 H), 7.80 (s, 1 H), 7.48 (s, 1 H), 6.95 (d, J=7 Hz, 1 H), 4.50-4.15 (m, 2 H), 1.32 (t, J=7 Hz, 3 H).

Workup

  1. customThe greenish reaction mixture
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. customThe phases were separated
  5. customas a precipitation that
  6. filtrationwas filtered off
  7. concentrationThe solvent was concentrated in vacuo and additional product
  8. customprecipitated
  9. filtrationthat was filtered

Sources & evidence

ORD record
ord-964d15afdedf4f14af64afdbd71d56d9
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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