Cesium carbonate → HCID 20767770, compound

HRID 985329Notes

Reaction equation

HRID 985329 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([O-:12])=[O:11])=[C:8]([CH3:13])[S:7][C:6]=2[CH:14]=1.Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]2[CH:22]=[C:23]([C:25]([N:27]3[CH2:31][CH2:30][C@@H:29]([O:32][CH3:33])[CH2:28]3)=[O:26])[S:24][C:17]=12.[C:34]([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:33][O:32][C@@H:29]1[CH2:30][CH2:31][N:27]([C:25]([C:23]2[S:24][C:17]3[C:18](=[N:19][CH:20]=[CH:21][C:16]=3[O:1][C:2]3[CH:3]=[CH:4][C:5]4[C:9]([C:10]([O:12][CH3:34])=[O:11])=[C:8]([CH3:13])[S:7][C:6]=4[CH:14]=3)[CH:22]=2)=[O:26])[CH2:28]1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207677657-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridineHCID 178435028HCID 178435028, compound

Product 1

HCID 20767770HCID 20767770, compoundYield 100%

Procedure

This material was prepared from the reaction of 6-hydroxy-2-methylbenzo[b]thiophene-3-carboxylate 11a (267 mg, 1.20 mmole) with 7-chloro-2-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridine 4b (297 mg, 1.00 mmole) and Cs2CO3 (977 mg, 3.00 mmole) in a manner similar to that previously described for example 1 to give a brown solid (480 mg, 100%). 1H NMR (DMSO-d6, 300 MHz) δ8.58 (1H, d, J=5.46 Hz), 8.39 (1H, d, J=8.85 Hz), 8.07 (1H, s), 8.02 (1H, d, J=2.26 Hz), 7.42 (1H, dd, J=2.35, 8.95 Hz), 6.79 (1H, d, J=5.46 Hz), 4.12-3.80 (3H, m), 3.91 (3H, s), 3.68-3.46 (2H, m), 3.27, 3.24 (3H, s), 2.82 (3H, s), 2.17-1.92 (2H, m).

Sources & evidence

ORD record
ord-474d0e76e3234e45936c4c189f1cddf4
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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