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

HRID 985192Notes

Reaction equation

HRID 985192 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): δ8.73 (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-bd0a15adfdc5405eac5505c2ec3aa248
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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