(R)-3-Pyrrolidinol → 7-chloro-2-[(R)-3-hydroxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridine

HRID 1825063Notes

Reaction equation

HRID 1825063 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O-:13])=O)[S:10][C:3]=12.[Li+].[OH:15][C@@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:18]3[CH2:19][CH2:20][C@@H:16]([OH:15])[CH2:17]3)=[O:13])[S:10][C:3]=12

Participants

3

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 23677819Lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate

Product 1

HCID 207677587-chloro-2-[(R)-3-hydroxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridineYield 36%

Procedure

This material was prepared by the coupling of lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate and (R)-3-hydroxypyrrolidine in a manner as previously described for example 2a to give 3.06 g (36%) of an off-white solid. 1H NMR (DMSO-d6): δ 8.73 (1H, d, J=5.1 Hz), 8.15, 8.09 (1H, s), 7.69 (1H, d, J=5.1 Hz), 5.10–5.06 (1H, m), 4.43–4.29 (1H, m), 4.05–3.89 (2H, m), 3.72–3.43 (2H, m), 2.08–1.79 (2H, m).

Sources & evidence

ORD record
ord-3e0502ee862d42f291e1858bb86b9013
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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