Cesium carbonate → HCID 22143662, compound

HRID 985229Notes

Reaction equation

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

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 221435306-hydroxy-N,1,2-trimethyl-1H-indole-3-carboxamide

HCID 221435377-Chloro-N,N-dimethylthieno[3,2-b]pyridine-2-carboxamide

Product 1

HCID 22143662HCID 22143662, compoundYield 73%

Procedure

This material was prepared by the reaction 7-chloro-N,N-dimethylthieno[3,2-b]pyridine-2-carboxamide 33a (0.077 g, 0.32 mmole) and 6-hydroxy-N,1,2-trimethyl-1H-indole-3-carboxamide 16e (0.070 g, 0.32 mmole) and Cs2CO3 (0.104 g, 0.32 mmole) in a manner as previously described for example 1 to give a pale yellow solid (0.098 g, 73%). 1H NMR (300 MHz, CD3OD) δ8.38 (1H, d, J=5.5 Hz), 7.75 (1H, d, J=8.7 Hz), 7.66 (1H, s), 7.28 (1H, d, J=2.1 Hz), 6.94 (1H, dd, J=2.1, 8.7 Hz), 6.60 (1H, d, J=5.5 Hz), 3.61 (3H, s), 3.21 (6H, m), 2.87 (3H, s), 2.56 (3H, s). ESIMS (MH+): 423.05.

Sources & evidence

ORD record: ord-6757a9d247104066a3a03254243b6f01
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869962B2

Reaction notes

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