Cesium carbonate → HCID 20767770, compound

HRID 1825072Notes

Reaction equation

HRID 1825072 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:22]=[CH:23][C:24]2[C:28]([C:29]([O:31][CH3:32])=[O:30])=[C:27]([CH3:33])[S:26][C:25]=2[CH:34]=1.C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:19][O:18][C@@H: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:22]=[CH:23][C:24]4[C:28]([C:29]([O:31][CH3:32])=[O:30])=[C:27]([CH3:33])[S:26][C:25]=4[CH:34]=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 22143531HCID 22143531, compound

Product 1

HCID 20767770HCID 20767770, compoundYield 43%

Procedure

Example 11(b) was prepared by the reaction of 7-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridine 4b (417 mg, 1.40 mmole) with methyl 6-hydroxy-2-methylbenzo[b]thiophene-3-carboxylate 11a (417 mg, 2.11 mmole) and Cs2CO3 (2.29 g, 7.02 mmole) in a manner as previously described for example 1 to give 290 mg (43%) of a yellow solid. 1H NMR (DMSO-d6): δ8.58 (1H, d, J=5.4 Hz), 8.39 (1H, d, J=9.0 Hz), 8.07 (1H, s), 8.02 (1H, d, J=2.3 Hz), 7.42 (1H, dd, J=2.3, 9.0 Hz), 6.79 (1H, d, J=5.4 Hz), 4.08–3.99 (3H, m), 3.87–3.86 (2H, m), 3.91 (3H, s), 3.64–3.59 (2H, m), 3.27, 3.24 (3H, s), 2.82 (3H, s).

Sources & evidence

ORD record
ord-d952da92a0ac4b1bb6e2436d3e9277f7
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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