Cesium carbonate → HCID 22143500, compound

HRID 985303Notes

Reaction equation

HRID 985303 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][C@@H:15]([O:18][CH3:19])[CH2:14]3)=[O:12])[S:10][C:3]=12.[OH:20][C:21]1[CH:34]=[CH:33][C:24]2[C:25]([C:29]([O:31][CH3:32])=[O:30])=[C:26]([CH3:28])[O:27][C:23]=2[CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:19][O:18][CH:15]1[CH2:16][CH2:17][N:13]([C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[O:20][C:21]3[CH:34]=[CH:33][C:24]4[C:25]([C:29]([O:31][CH3:32])=[O:30])=[C:26]([CH3:28])[O:27][C:23]=4[CH:22]=3)[CH:8]=2)=[O:12])[CH2:14]1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207677657-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridineHCID 22143518Methyl 6-hydroxy-2-methylbenzofuran-3-carboxylate

Product 1

HCID 22143500HCID 22143500, compoundYield 58.5%

Procedure

This material was prepared by the reaction of 7-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridine 4b (707 mg, 2.38 mmole) with methyl 6-hydroxy-2-methyl-benzofuran-3-carboxylate 89c (565 mg, 2.74 mmole) and Cs2CO3 (3.10 g, 9.53 mmole) in a manner as previously described for example to give 650 mg (58%) of an off-white solid. 1H NMR (DMSO-d6) δ8.57 (1H, d, J=5.3 Hz), 8.07 (1H, s), 7.96 (1H, d, J=8.6 Hz), 7.75 (1H, d, J=2.0 Hz), 7.31 (1H, dd, J=8.6, 2.0 Hz), 6.74 (1H, d, J=5.6 Hz), 4.10-3.85 (3H, m), 3.90 (3H, s), 3.65-3.45 (2H, m), 3.25 (3H, d, J=12.6 Hz), 2.77 (3H, s), 2.15-1.95 (2H, m).

Sources & evidence

ORD record
ord-c5ee5d48348240a198090359ba8d5c02
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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