Dimethylformamide → HCID 59700619, compound

HRID 902021Notes

Reaction equation

HRID 902021 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:15]([C:16]2[C:25]3[C:20](=[CH:21][C:22]([OH:26])=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)=[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][N:9]2[N:8]=1.CN(C=O)C.Br[CH2:33][CH2:34][Cl:35].C(=O)([O-])[O-].[Cs+].[Cs+]>CO>[Cl:35][CH2:34][CH2:33][O:26][C:22]1[CH:21]=[C:20]2[C:25]([C:16]([C:15]3[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[N:8][N:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=34)=[CH:17][CH:18]=[N:19]2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78491-Bromo-2-ChloroethaneHCID 10796Cesium carbonateHCID 135983747HCID 135983747, compound

Product 1

HCID 59700619HCID 59700619, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

4-(2-Pyridin-2-yl-pyrazolo[1,5-a]pyridin-3-yl)-quinolin-7-ol in a solution of DMF and MeOH was treated with 1-bromo-2-chloroethane (3 equiv) and cesium carbonate (2 equiv). The reaction was heated to 60° C. and stirred overnight. As described above, the desired product was then obtained upon chromatographic purification (EtOAc, followed by MeOH, then 2 M NH3 in MeOH). Yield; 30% overall from Prep. 90. MS ES+ m/e 401.0 (M+1).

Sources & evidence

ORD record
ord-d7940a90f7e0431eac37fc5bb250248f
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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