Sodium hydride → HCID 66914145, compound

HRID 2104802Notes

Reaction equation

HRID 2104802 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:28][C:29]1[CH:30]=[C:31]([CH:34]=[C:35](F)[CH:36]=1)[C:32]#[N:33]>CN1C(=O)CCC1>[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[O:24][C:35]1[CH:34]=[C:31]([CH:30]=[C:29]([Br:28])[CH:36]=1)[C:32]#[N:33])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27833303-Bromo-5-fluorobenzonitrileHCID 66524287HCID 66524287, compound

Product 1

HCID 66914145HCID 66914145, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

3-(3-benzyl-8-chloroquinolin-4-yl)phenol (0.100 g, 0.289 mmol) was taken into NMP (1 mL) and to this was added NaH (0.0127 g, 0.318 mmol, 60% dispersion in oil) and stirred for 15 minutes. 3-Bromo-5-fluorobenzonitrile (0.116 g, 0.578 mmol) was added and the reaction was heated at 160° C. overnight. The reaction was cooled and quenched with water followed by extraction with ether. After drying and concentration the product was purified via Prep HPLC using 10-100% v acetonitrile in water as the eluent to yield 0.028 g of product. MS (ESI) m/z 526 ([M+H])+.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with water
  3. extractionfollowed by extraction with ether
  4. customAfter drying
  5. concentrationconcentration the product
  6. customwas purified via Prep HPLC

Sources & evidence

ORD record
ord-f158c71cf93c47a5a82af4f217a5d60d
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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