Triethylsilane → HCID 53246150, compound

HRID 1189572Notes

Reaction equation

HRID 1189572 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH2:13]C)[N:10]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:9]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.FC(S(O[Si](C)(C)C)(=O)=O)(F)F.C([SiH](CC)CC)C.[C:46]1([S:52]([C:55]2[CH:62]=[CH:61][CH:60]=[CH:59][C:56]=2[CH:57]=O)(=[O:54])=[O:53])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:57][C:56]3[CH:59]=[CH:60][CH:61]=[CH:62][C:55]=3[S:52]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)(=[O:54])=[O:53])=[C:11]([CH3:13])[N:10]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:9]=2[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 6409162-(phenylsulfonyl)benzaldehydeHCID 67238441HCID 67238441, compound

Product 1

HCID 53246150HCID 53246150, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Ethyl 2-(3-(4-fluorophenyl)-5-ethyl-2-phenyl-1H-pyrrol-1-yl)acetate (0.8 g, 2.371 mmol) was dissolved in 10 mL DCM and cooled to −78° C. Trimethylsilyl trifluoromethylsulfonate (0.964 ml, 5.34 mmol) was then added, followed by triethylsilane (1.136 ml, 7.11 mmol). The reaction mixture was stirred at −78° C. for 30 minutes. At this time, 2-(phenylsulfonyl)benzaldehyde (0.876 g, 3.56 mmol) was added portion-wise as a solution in 2.0 mL DCM. The reaction was monitored by LC/MS. Following addition of the aldehyde, the cold bath was removed and the mixture was stirred overnight (gradually warming to room temp). The reaction was quenched with sodium bircarbonate and moved to a separatory funnel. Layers were separated and the aqueous portion was extracted two additional times with DCM. The organics were combined, dried, filtered, and concentrated. The resulting crude oil was purified via column chromatography (SiO2) using a 0-40% EtOAc/hexane gradient to give ethyl 2-(3-(4-fluorophenyl)-5-methyl-2-phenyl-4-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (1.0 g, 1.762 mmol, 74.3% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 8.31-8.29 (m, 1H), 7.80-7.78 (m, 2H), 7.53-7.49 (m, 2H), 7.43-7.36 (m, 3H), 7.25-7.21 (m, 4H), 7.10-7.07 (m, 2H), 6.60-6.56 (m, 2H), 6.52-6.48 (m, 2H), 4.49 (s, 2H), 4.21 (q, 2H), 3.97 (s, 2H), 1.86 (s, 3H), 1.26 (t, 3H).

Workup

  1. customthe cold bath was removed
  2. stirringthe mixture was stirred overnight (
  3. temperaturegradually warming to room temp)
  4. customThe reaction was quenched with sodium bircarbonate
  5. custommoved to a separatory funnel
  6. customLayers were separated
  7. extractionthe aqueous portion was extracted two additional times with DCM
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting crude oil was purified via column chromatography (SiO2)

Sources & evidence

ORD record
ord-e195bfce987e46298ea92bad3787948f
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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