Sodium hydride → HCID 54689886, compound

HRID 1244143Notes

Reaction equation

HRID 1244143 reaction equation
C(O[C:4]([C:6]1[C:7]([C:17]2[S:18][C:19]([I:23])=[C:20]([CH3:22])[CH:21]=2)=[CH:8][S:9][C:10]=1[NH:11][C:12](=[O:16])[CH2:13][C:14]#[N:15])=[O:5])C.[H-].[Na+]>C1COCC1.CN(C=O)C>[OH:5][C:4]1[C:6]2[C:7]([C:17]3[S:18][C:19]([I:23])=[C:20]([CH3:22])[CH:21]=3)=[CH:8][S:9][C:10]=2[NH:11][C:12](=[O:16])[C:13]=1[C:14]#[N:15]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69607335HCID 69607335, compound

Product 1

HCID 54689886HCID 54689886, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To 5′-(2-Cyano-acetylamino)-5-iodo-4-methyl-[2,3′]bithiophenyl-4′-carboxylic acid ethyl ester (1.7 g, 3.7 mmol, Example 222 d) in THF : DMF (1:1, 18.5 ml) under N2 at 0° C. was added NaH (95%, 442 mg, 18.5 mmol). The suspension was allowed to warm to rt with stirring overnight. The reaction was quenched with H2O. The mixture was placed in a separatory funnel, overwhelmed with H2O and extracted with EtOAc. Most of the color is removed with this washing step. The aqueous layer was acidified with 6 M HCl and a solid ppt out which was collected by filtration to give 4-hydroxy-3-(5-iodo-4-methylthien-2-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (880 mg, 2.1 mmol, 58%); MS (ESI) m/z 415.0 (M+H+); 1H NMR (300 MHz, DMSO-d6) δ ppm 7.32 (s, 1H), 7.04 (s, 1H), 6.86 (s, 1H), 2.13 (s, 3H).

Workup

  1. customat 0° C.
  2. customThe reaction was quenched with H2O
  3. customThe mixture was placed in a separatory funnel
  4. extractionextracted with EtOAc
  5. customMost of the color is removed with this washing step
  6. filtrationa solid ppt out which was collected by filtration

Sources & evidence

ORD record
ord-8cb094706ddb4be699ff03f5790aed8a
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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