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Sodium hydride → HCID 69417907, compound

HRID 1594504
Notes
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Reaction equation

HRID 1594504 reaction equation
[Cl:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]2[NH:6][C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([CH:16]4[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)=[CH:12][CH:11]=3)=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:27][O:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][C:33]([CH2:36]Br)=[CH:32][CH:31]=1>CN(C=O)C.[NH4+].[Cl-]>[Cl:24][C:23]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]([CH2:36][C:33]3[CH:34]=[CH:35][C:30]([C:29]([O:28][CH3:27])=[O:38])=[CH:31][CH:32]=3)[C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([CH:16]4[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)=[CH:14][CH:15]=3)=[N:6][C:5]=2[CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 69417851HCID 69417851, compound

Product 1

HCID 69417907HCID 69417907, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517
Ammonium Chloride
Solvent

Procedure

To the title compound of Example 4, Step A (1.1 mmol, 400 mg) in DMF (2 mL) was added NaH (1.2 mmol, 49 mg of 60% suspension in mineral oil). After 25 min methyl-4-(bromomethyl)benzoate (1.2 mmol, 280 mg) was added and the reaction mixture was allowed to stand at ambient temperature for 30 min. The reaction was diluted with saturated NH4Cl (5 mL), and the crude product was extracted into EtOAc. The organic phase was dried with Na2SO4 and concentrated in vacuo. Flash chromatography on silica eluting with 15% EtOAc in hexanes afforded the product as a yellow solid. LC-MS (ESI, Method C): 4.44 min, m/z 508.1 (M+1).

Workup

  1. extractionthe crude product was extracted into EtOAc
  2. dry with materialThe organic phase was dried with Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dea37ce218fe4fea82bbd165579833ef
Source dataset
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07301036B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes