4-Iodophenylisothiocyanate → Ethyl 2-(4-iodophenylamino)thieno[2,3-b]pyridine-3-carboxylate

HRID 1944065

Reaction equation

HRID 1944065 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[I:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[S:23])=[CH:17][CH:16]=1>>[CH2:12]([O:11][C:9]([C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[S:23][C:22]=1[NH:21][C:18]1[CH:19]=[CH:20][C:15]([I:14])=[CH:16][CH:17]=1)=[O:10])[CH3:13]

Participants

3

Reactant 2

HCID 749384-IodophenylisothiocyanateHCID 15326671Ethyl 2-(2-chloropyridin-3-yl)acetate

Product 1

HCID 24739705Ethyl 2-(4-iodophenylamino)thieno[2,3-b]pyridine-3-carboxylate

Procedure

Prepared from ethyl (2-chloropyridin-3-yl)acetate (D. H. Bremner et al., Synthesis, 1997, 949) (750 mg, 3.8 mmol) and 4-iodophenyl isothiocyanate (1.0 g, 3.8 mmol) by the method of Example 1. Title compound obtained as an off-white solid (800 mg, 50%). δH (DMSO-d6) 10.34 (1H, br s), 8.33-8.30 (2H, m), 7.79 (2H, dt, J 2.0, 6.7 Hz), 7.43-7.31 (3H, m), 4.40 (2H, q, J=7.1 Hz), 1.40 (3H, t, J=7.1 Hz). LCMS (ES+) RT 4.31 minutes, 425 (M+H)+.

Sources & evidence

ORD record
ord-8102850bae274dd0ac83ad9df8efc922
Source dataset
uspto-grants-2013_03
Patent number
US08394822B2

Linked notes

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