Pyridine → HCID 10369400, compound

HRID 2106059Notes

Reaction equation

HRID 2106059 reaction equation
[N:1]1([CH2:11][C:12]([OH:30])([CH2:17][C:18]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[O:28][CH3:29])([CH3:20])[CH3:19])[C:13]([F:16])([F:15])[F:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[O:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[C:42](Cl)=[O:43]>ClCCl>[F:27][C:25]1[CH:24]=[CH:23][C:22]([O:28][CH3:29])=[C:21]([C:18]([CH3:20])([CH3:19])[CH2:17][C:12]([OH:30])([C:13]([F:14])([F:15])[F:16])[CH2:11][N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]([C:42]([C:38]3[O:37][CH:41]=[CH:40][CH:39]=3)=[O:43])[CH2:3][CH2:2]2)[CH:26]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 682422-Furancarbonyl chlorideHCID 57809838HCID 57809838, compound

Product 1

HCID 10369400HCID 10369400, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(3,4-dihydro-2H-quinoxalin-1-ylmethyl)-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol (0.50 g, 0.117 mmol) in dichloromethane (10 mL) was added pyridine (0.24 mL, 0.129 mmol) and 2-furoyl chloride (0.012 mL, 0.129 mmol). The reaction was stirred at room temperature for 14 hours. The reaction mixture was diluted with dichloromethane, washed with two 25 mL portions of a saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered, and the solvent was evaporated in vacuo. Purification by flash column chromatography (5% MeOH/CH2Cl2) yielded the title compound as a white solid (14.5 mg).

Workup

  1. washwashed with two 25 mL portions of a saturated aqueous sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated in vacuo
  5. customPurification by flash column chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c2550d0eb31241c3afd24a88cde194d2
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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