Cesium carbonate → HCID 22143653, compound

HRID 985319Notes

Reaction equation

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

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 22143531HCID 22143531, compound

HCID 221435637-chloro-2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridine

Product 1

HCID 22143653HCID 22143653, compoundYield 61.2%

Procedure

This material was prepared from the reaction of methyl 6-hydroxy-2-methylbenzo[b]thiophene-3-carboxylate 11a (200 mg, 0.90 mmole) with 7-chloro-2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridine 1e (188 mg, 0.75 mmole) and Cs2CO3 (1.22 g, 3.75 mmole) in a manner as previously described for example 1 to give a yellow solid (200 mg, 51%). 1H NMR (DMSO-d6, 300 MHz) δ8.52 (1H, d, J=5.46 Hz), 8.38 (1H, d, J=9.04 Hz), 8.02 (1H, d, J=2.26 Hz), 7.89 (1H. s), 7.40 (2H, s), 7.02 (1H, s), 6.73 (1H, d, J=5.46 Hz), 3.98 (3H, s), 3.91 (3H, s), 2.82 (3H, s).

Sources & evidence

ORD record: ord-ab051732f0fe41b398f1eccb75caa282
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869962B2

Reaction notes

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