Water → HCID 58001449, compound

HRID 548988Notes

Reaction equation

HRID 548988 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[Cl:9].[H-].[Na+].[CH2:12]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20]2[C:23]3[C:24](=[C:26]([O:42][CH3:43])[CH:27]=[CH:28][C:29]=3[C:30](OC3C=CC([N+]([O-])=O)=CC=3)=[O:31])[O:25][C:19]=2[CH2:18]1)=[O:16])[CH3:13].O>CN(C=O)C>[Cl:9][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([Cl:8])[C:2]=1[NH:1][C:30]([C:29]1[CH:28]=[CH:27][C:26]([O:42][CH3:43])=[C:24]2[O:25][C:19]3[CH2:18][N:17]([C:15]([O:14][CH2:12][CH3:13])=[O:16])[CH2:22][CH2:21][C:20]=3[C:23]=12)=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 66592786HCID 66592786, compound

Product 1

HCID 58001449HCID 58001449, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-amino-3,5-dichloro pyridine (0.125 g, 0.765 mmol) in dry DMF, sodium hydride (0.0162 g, 0.675 mmol) was added at 0° C. followed by 4-nitrophenyl 2-(ethoxycarbonyl)-8-methoxy-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine-5-carboxylate (0.197 g, 0.45 mmol). Water was added to RM. Solid filtered out and purified on Silica Gel column with CHCl3: EtOAc to yield N-(3,5-dichloropyridin-4-yl)-2-(ethoxycarbonyl)-8-methoxy-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine-5-carboxamide.

Workup

  1. filtrationSolid filtered out
  2. custompurified on Silica Gel column with CHCl3

Sources & evidence

ORD record
ord-1473d6154ef940dcbfb1e26363364b42
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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