Dimethylformamide → HCID 58388096, compound

HRID 2080257Notes

Reaction equation

HRID 2080257 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].C1(OC(=O)NC[C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:24][CH:23]=2)C=CC=CC=1.[CH3:36][N:37](C)[CH:38]=[O:39]>[Cl-].[Na+].O>[O:28]([C:25]1[CH:26]=[C:27]([CH:22]=[CH:23][CH:24]=1)[CH2:36][NH:37][C:38]([N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)=[O:39])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 92264-AzaindoleHCID 24758Sodium hydrideHCID 67119602HCID 67119602, compound

Product 1

HCID 58388096HCID 58388096, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

1H-Pyrrolo[3,2-b]pyridine described in Preparation Example S-4 (44 mg, 0.37 mmol) was dissolved in N,N-dimethylformamide (3 mL), sodium hydride (18 mg, 0.45 mmol, 60% in oil) was added thereto, followed by stirring at room temperature for 30 minutes. Next, (4-phenoxy-benzyl)-carbamic acid phenyl ester described in Preparation Example 75 (143 mg, 0.45 mmol) was added, and the solution was stirred at room temperature for 2 hours. After the reaction was completed, the reaction solution was poured into brine, which was then extracted with ethyl acetate, and concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1), and the title compound (11 mg, 0.032 mmol, 8.7%) was obtained.

Workup

  1. additionwas added
  2. stirringthe solution was stirred at room temperature for 2 hours
  3. extractionwas then extracted with ethyl acetate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-b9d9712fe53f4c0890f08139e0d350c3
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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