Sodium hydride → HCID 86695946, compound

HRID 2369545Notes

Reaction equation

HRID 2369545 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[CH:11][N:12]=[C:13]([NH:16][C:17](=O)[CH3:18])[CH:14]=3)[CH:9]([CH3:20])[O:8][C:6]=2[CH:7]=1.[H-].[Na+].[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[CH:11][N:12]=[C:13]([N:16]([CH2:29][C:28]4[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[CH:26][CH:27]=4)[CH2:17][C:18]4[CH:2]=[CH:7][C:6]([O:8][CH3:9])=[CH:5][CH:4]=4)[CH:14]=3)[CH:9]([CH3:20])[O:8][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 86695947HCID 86695947, compound

Product 1

HCID 86695946HCID 86695946, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-(8-chloro-5-methyl-5H-chromeno[3,4-c]pyridin-2-yl)acetamide (250 mg, 0.866 mmol) in DMF (25 mL) was added NaH (62.3 mg, 2.60 mmol) at room temperature and stirred for 10 min. 4-Methoxybenzyl chloride (0.236 mL, 1.732 mmol) was added dropwise and stirred at room temperature overnight. The reaction was quenched with ice and extracted with ethyl acetate (25 mL). The organic layer was separated, washed with water (25 mL), brine (25 mL), dried over sodium sulphate and concentrated under reduced pressure to afford 8-chloro-N,N-bis(4-methoxybenzyl)-5-methyl-5H-chromeno[3,4-c]pyridin-2-amine (200 mg, 0.20 mmol, 24% yield) as a yellow oil. This was taken to the next step without purification. LCMS (ESI) m/e 487.2 [(M±H)+, calcd for C29H28ClN2O3 487.2]; LC/MS retention time (Method C): tR=2.52 min.

Workup

  1. stirringstirred at room temperature overnight
  2. customThe reaction was quenched with ice
  3. extractionextracted with ethyl acetate (25 mL)
  4. customThe organic layer was separated
  5. washwashed with water (25 mL), brine (25 mL)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-537f3ecbd1b847aa98d6246820d516cb
Source dataset
uspto-grants-2014_04
Patent number
US08703953B2

Reaction notes

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