Boron trifluoride etherate → HCID 58963165, compound

HRID 917534Notes

Reaction equation

HRID 917534 reaction equation
[CH2:1]([C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH3:12])[C:7]=2[CH:6]=[C:5]([CH:13]=O)[CH:4]=1)[CH3:2].[NH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.S(C[N+]#[C-])(C1C=CC(C)=CC=1)(=O)=[O:25].B(F)(F)F.[O:41]([CH2:44]C)[CH2:42]C>O.CO>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([NH:15][CH:13]([C:5]2[CH:4]=[C:3]([CH2:1][CH3:2])[C:11]3[O:10][CH:9]=[C:8]([CH3:12])[C:7]=3[CH:6]=2)[C:42]([O:41][CH3:44])=[O:25])=[CH:17][CH:18]=1)#[N:21]

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 133964-AminobenzonitrileHCID 161915Tosylmethyl isocyanideHCID 58963161HCID 58963161, compound

Product 1

HCID 58963165HCID 58963165, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

7-Ethyl-3-methylbenzofuran-5-carbaldehyde 32 (2 g, 10.9 mmole), dry methanol (40 ml), and 4-aminobenzonitrile (1.42 g, 12 mmoles) were combined and heated to reflux under a nitrogen atmosphere. The reaction was refluxed for 2.5 hours and then cooled to room temperature. Tosylmethylisonitrile (2.12 g, 10.0 mmoles) was added with 9 ml methanol. The reaction mixture was cooled to 0° C. and BF3-OEt2 was added drop wise over 40 minutes. The reaction was allowed to stir for 2 hours and water (2 ml) was added and the reaction stirred for at least 1 hour. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and aqueous citric acid. The organic layer was separated, washed with brine, dried over sodium sulfate and the solvent removed in vacuo. The crude product was purified by flash chromatography (25% ethyl acetate in hexanes) to yield 2.19 g of methyl 2-(4-cyanophenylamino)-2-(7-ethyl-3-methylbenzofuran-5-yl)acetate 5.

Workup

  1. temperatureheated
  2. temperatureto reflux under a nitrogen atmosphere
  3. temperatureThe reaction was refluxed for 2.5 hours
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. stirringthe reaction stirred for at least 1 hour
  6. customThe solvent was removed in vacuo
  7. customthe residue partitioned between ethyl acetate and aqueous citric acid
  8. customThe organic layer was separated
  9. washwashed with brine
  10. dry with materialdried over sodium sulfate
  11. customthe solvent removed in vacuo
  12. customThe crude product was purified by flash chromatography (25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1c7d0e280f60467ea4a4d3c09bdb6473
Source dataset
uspto-grants-2007_09
Patent number
US07273886B2

Reaction notes

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