Cesium carbonate → HCID 20767929, compound

HRID 1825145Notes

Reaction equation

HRID 1825145 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][CH:13]=[CH:14][N:15]=3)[S:10][C:3]=12.[OH:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21]([C:28]([NH:30][CH:31]([CH3:33])[CH3:32])=[O:29])=[C:22]([CH3:27])[N:23]2[CH3:26])=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>>[CH:31]([NH:30][C:28]([C:21]1[C:20]2[C:24](=[CH:25][C:17]([O:16][C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[CH:8]=[C:9]([C:11]5[S:12][CH:13]=[CH:14][N:15]=5)[S:10][C:3]=34)=[CH:18][CH:19]=2)[N:23]([CH3:26])[C:22]=1[CH3:27])=[O:29])([CH3:33])[CH3:32]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 221436637-Chloro-2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridineHCID 22143669HCID 22143669, compound

Product 1

HCID 20767929HCID 20767929, compoundYield 38%

Procedure

This material was prepared by the reaction 7-chloro-2-(1,3-thiazol-2-yl)thieno[3,2-b]pyridine 41a (0.084 g, 0.33 mmole) with 6-hydroxy-N-isopropyl-1,2-dimethyl-1H-indole-3-carboxamide 66b (0.082 g, 0.33 mmole) and Cs2CO3 (0.116 g, 0.33 mmole) to give a off-white solid (0.058 g, 38%). 1H NMR (300 MHz, CDCl3) δ 8.46 (1H, d, J=5.4 Hz), 7.93 (1H, s), 7.88 (1H, d, J=3.2Hz), 7.73 (1H, d, J=8.6 Hz), 7.42 (1H, d, J=3.2 Hz), 7.17 (1H, d, J=2.1 Hz), 7.07 (1H, dd, J=2.1, 8.6 Hz), 6.54 (1H, d, J=5.4 Hz), 5.71 (1H, d, J=7.7 Hz), 4.36 (1H, m), 3.66 (3H, s), 2.72 (3H, s), 1.31 (6H, d, J=6.6 Hz); ESIMS (MH+): 463.10.

Sources & evidence

ORD record
ord-56b1b868e2714b9bba97fed1f2fb6c76
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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