Methyl Thioglycolate → Methyl 3-amino-5-(pyridin-4-yl)thiophene-2-carboxylate

HRID 2363920Notes

Reaction equation

C[O-].[Na+].[C:4]([O:8][CH3:9])(=[O:7])[CH2:5][SH:6].Cl[C:11]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)=[CH:12][C:13]#[N:14]>CO>[NH2:14][C:13]1[CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[S:6][C:5]=1[C:4]([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of sodium methoxide (2.12 g, 39.3 mmol) in methanol (59 mL) was added methyl thioglycolate (3.51 mL, 39.3 mmol). After 10 min, 3-chloro-3-(pyridin-4-yl)acrylonitrile (6.47 g, 39.3 mmol) was added, and the mixture was heated at 50° C. After 1 h, the mixture was concentrated to about a half volume at reduced pressure and poured into water (500 mL). Extraction with ethyl acetate/tetrahydrofuran (4:1, 500 mL), washing with brine, drying over magnesium sulfate, filtration and concentration at reduced pressure gave the title compound (8.81 g, 96%) as a yellow solid:

Workup

waitAfter 1 h
concentrationthe mixture was concentrated to about a half volume at reduced pressure
additionpoured into water (500 mL)
extractionExtraction with ethyl acetate/tetrahydrofuran (4:1, 500 mL)
washwashing with brine
dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure

Sources & evidence

ORD record: ord-d49089ce8789475686828437076fe202
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

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