Sodium hydride → HCID 67071698, compound

HRID 1260531Notes

Reaction equation

HRID 1260531 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C@@H:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=1>CN(C=O)C>[CH3:11][C@H:10]([NH:12][C:13](=[O:15])[CH3:14])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 67071697HCID 67071697, compound

Product 1

HCID 67071698HCID 67071698, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N—[(S)-3-(4-Hydroxyphenyl)-1-methylpropyl]acetamide (770 mg, 3.72 mmol) and sodium hydride (55% in oil, 243 mg, 5.57 mmol) were stirred in 30 ml of DMF under argon at room temperature for 30 min. Following addition of 2-chloro-5-nitropyridine (648 mg, 4.09 mmol) the mixture was stirred at 80° C. for 1.5 h, concentrated, and mixed with ethyl acetate and water, and the organic phase was separated off and concentrated. The crude product was further reacted without purification.

Workup

  1. concentrationconcentrated
  2. additionmixed with ethyl acetate and water
  3. customthe organic phase was separated off
  4. concentrationconcentrated
  5. customThe crude product was further reacted without purification

Sources & evidence

ORD record
ord-3a0c5c826d3846f18b356a038d0f5db2
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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