Dimethylformamide → HCID 69516488, compound

HRID 855095Notes

Reaction equation

HRID 855095 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1.[CH3:21][C:22]([CH3:27])([CH3:26])[CH2:23]CN.C([O-])([O-])=O.[K+].[K+].C[N:35](C=O)C>>[CH2:23]([NH:35][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1)[C:22]([CH3:26])([CH3:21])[CH3:27]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 197093,3-DimethylbutylamineHCID 58934808ethyl 7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69516488HCID 69516488, compound

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl 7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate (Example 612a, Step 2) (0.45 g, 1.54 mmole) and 3,3-dimethylbutylamine (0.13 g, 1.54 mmole) was dissolved in anhydrous DMF (5 mL), warmed to 90° C. and treated with K2CO3 (0.25 g, 1.84 mmole). The mixture was maintained at 90° C. for 24 hrs, cooled to room temperature, filtered through celite and condensed to a viscous oil (0.55g, 98%). No further purification was performed. LCMS m/z 358.00 (M+H).

Workup

  1. temperatureThe mixture was maintained at 90° C. for 24 hrs
  2. temperaturecooled to room temperature
  3. filtrationfiltered through celite and condensed to a viscous oil (0.55g, 98%)
  4. customNo further purification

Sources & evidence

ORD record
ord-aef9c18c1a9940df9c8d39356ea78b36
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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