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Dimethylformamide → HCID 59700613, compound

HRID 902020
Notes
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Reaction equation

HRID 902020 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][CH2:35][Cl:36].C(=O)([O-])[O-].[Cs+].[Cs+]>CO>[Cl:36][CH2:35][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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 135983747HCID 135983747, compound

Product 1

HCID 59700613HCID 59700613, compound

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

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 is treated with 1-bromo-3-chloropropane (3 equiv) and cesium carbonate (2 equiv). The reaction is heated to 60° C. and stirred overnight. The reaction is then purified on silica gel column (see Prep. 77) chromatography to afford the desired product.

Workup

  1. customThe reaction is then purified on silica gel column (see Prep. 77) chromatography

Sources & evidence

ORD record
ord-4dbb74bec96844eeae798d9b6b163225
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07365066B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes