3-AMINO-4-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER synthesis

5synthesis methods

Product Name:3-AMINO-4-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
CAS Number:35212-88-5
Molecular formula:C11H11NO3S
Molecular Weight:237.27

94088-46-7
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$16.00/25g

2365-48-2 Synthesis

2365-48-2
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$14.00/25g

3-AMINO-4-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER

35212-88-5
26 suppliers
$75.00/250mg

Yield:35212-88-5 83%

Reaction Conditions:

with NaH in dimethyl sulfoxide;

Steps:

18 4-(3-Bromoanilino)-9-methoxybenzo[b]thieno[3,2-d]pyrimidine hydrochloride.

Methyl 3-amino-4-methoxybenzothiophene-2-carboxylate. Methyl thioglycollate (0.18 mL, 1.9 mmol) is added dropwise to a suspension of NaH (60% oil suspension, 176 mg, 4.4 mmol) in DMSO (5 mL), stirred under N₂ at 25° C. When gas evolution ceases, 2-fluoro-6-methoxybenzonitrile (266 mg, 1.76 mmol) in DMSO 5 mL is added in one portion. After 3 h, the reaction mixture is poured onto ice-water, and the beige precipitate is collected by suction filtration, rinsed and air dried to give methyl 3-amino-4-methoxybenzothiophene-2-carboxylate (345 mg, 83%). ¹ H NMR (DMSO) δ7.44-7.37 (2H, m), 7.00, (2H brs), 6.90 (1H, d, J=7.7Hz), 3.95 (3H, s), 3.76 (3H, s).

References:

US5679683,1997,A

886362-07-8 Synthesis