Isoamyl Nitrite → HCID 21942337, compound

HRID 2216399Notes

Reaction equation

HRID 2216399 reaction equation
N[C:2]1[C:10]2[C:5](=[N:6][C:7]([CH:11]([CH3:13])[CH3:12])=[CH:8][CH:9]=2)[S:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].N(OCCC(C)C)=O>O1CCCC1>[CH:11]([C:7]1[N:6]=[C:5]2[S:4][C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:2][C:10]2=[CH:9][CH:8]=1)([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 21942355HCID 21942355, compound

Product 1

HCID 21942337HCID 21942337, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

3-Cyano-6-isopropyl-2-mercaptopyridine (50 g) synthesized according to U.S. Pat. No. 5,001,137 (Mar. 19, 1991), sodium ethoxide (22.9 g) and bromoethyl acetate (34.2 ml) were added to ethanol (500 ml) and the mixture was stirred at room temperature for 1 hr and the solvent was evaporated. The residue was recrystallized from ethanol to give ethyl 3-amino-6-isopropylthieno[2,3-b]pyridine-2-carboxylate (69.3 g) (melting point: 161-162° C.). (2) This ester (30 g) and isoamyl nitrite (45.7 ml) were added to tetrahydrofuran (300 ml) and the mixture was stirred at 60° C. for 2 hr and the solvent was evaporated under reduced pressure. The residue was separated and purified by silica gel column chromatography (mobile phase; chloroform) to give ethyl 6-isopropylthieno[2,3-b]pyridine-2-carboxylate (7.1 g). melting point: 73-74° C. (3) This was subjected to hydrolysis under basic conditions according to a conventional method to give the title compound (5.8 g). melting point: 218-220° C.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was separated
  3. custompurified by silica gel column chromatography (mobile phase; chloroform)

Sources & evidence

ORD record
ord-9815aa6bba9a44d3a5f8c0255741943e
Source dataset
uspto-grants-2006_09
Patent number
US07112594B2

Reaction notes

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