Dimethylformamide → HCID 69517027, compound

HRID 855078Notes

Reaction equation

HRID 855078 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[O:8][CH:7]([C:13]([F:16])([F:15])[F:14])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5]2.[CH3:22][C:23]([CH3:28])([CH3:27])[CH2:24]CN.C([O-])([O-])=O.[K+].[K+].C[N:36](C=O)C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[NH:36][CH2:24][C:23]([CH3:27])([CH3:22])[CH3:28])[O:8][CH:7]([C:13]([F:16])([F:15])[F:14])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5]2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 197093,3-DimethylbutylamineHCID 21883602ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69517027HCID 69517027, compound

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate (Example 7a, Step 2) (0.5 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 (0.6g, 98%). No further purification was performed: GCMS m/z 391.00 (M+).

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 (0.6g, 98%)
  4. customNo further purification

Sources & evidence

ORD record
ord-8867bcbfcba242ebba758a4d86ef1a50
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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