Dimethylformamide → HCID 58961593, compound

HRID 916965Notes

Reaction equation

HRID 916965 reaction equation
CN(C=O)C.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]1[NH:19][C:18](=[O:20])[C:17]([C:21]([O:23][CH3:24])=[O:22])=[CH:16][C:15]=1[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].[F:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1[F:47])[CH2:42]Br>C(OCC)(=O)C>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]1[C:15]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[CH:16][C:17]([C:21]([O:23][CH3:24])=[O:22])=[C:18]([O:20][CH2:42][C:41]2[CH:44]=[CH:45][C:46]([F:47])=[C:39]([F:38])[CH:40]=2)[N:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 69417262HCID 69417262, compound

Product 1

HCID 58961593HCID 58961593, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an oven-dried round bottom flask was added DMF (5 mL), the product of Step E (0.500 g; 1.27 mmol), Cs2CO3 (0.910 g; 2.79 mmol), and 3,4-difluorobenzyl bromide (0.162 mL; 1.27 mmol). The reaction was stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate and washed with saturated aq. NaHCO3 solution (3×), and brine. The organic portion was dried (Na2SO4), filtered, and concentrated in vacuo. Purification done by MPLC (silica gel; 0-10% ethyl acetate/hexane gradient) afforded the desired product: m/e=518 (M+1).

Workup

  1. washwashed with saturated aq. NaHCO3 solution (3×), and brine
  2. dry with materialThe organic portion was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-9ec3c7d63acf4fdb98e6417d71f85115
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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