1-Acetoxy-2-bromoethane → HCID 21942355, compound

HRID 2216398Notes

Reaction equation

HRID 2216398 reaction equation
[C:1]([C:3]1[C:4]([SH:12])=[N:5][C:6]([CH:9]([CH3:11])[CH3:10])=[CH:7][CH:8]=1)#[N:2].[O-]CC.[Na+].[C:17]([O:20][CH2:21][CH2:22]Br)(=[O:19])[CH3:18]>C(O)C>[NH2:2][C:1]1[C:3]2[C:4](=[N:5][C:6]([CH:9]([CH3:10])[CH3:11])=[CH:7][CH:8]=2)[S:12][C:18]=1[C:17]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 135641-Acetoxy-2-bromoethaneHCID 2723922Sodium ethoxideHCID 178439151HCID 178439151, compound

Product 1

HCID 21942355HCID 21942355, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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
  2. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-88754221eb364f4b96405139b28a920d
Source dataset
uspto-grants-2006_09
Patent number
US07112594B2

Reaction notes

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