Triethylsilane → HCID 53246500, compound

HRID 1189580Notes

Reaction equation

HRID 1189580 reaction equation
C([SiH](CC)CC)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[CH3:20][C:21]1[N:22]([CH2:48][C:49]([O:51][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[O:50])[C:23]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=2)=[CH:24][C:25]=1[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=[O:35])=[O:34].[CH3:59][C:60]1[N:61]([CH2:87][C:88]([O:90]CC2C=CC=CC=2)=[O:89])[C:62]([C:81]2[CH:82]=[N:83][CH:84]=[CH:85][CH:86]=2)=[CH:63][C:64]=1[CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=1[S:72]([C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)(=[O:74])=[O:73]>CO.[Pd]>[CH3:20][C:21]1[N:22]([CH2:48][C:49]([O:51][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[O:50])[C:23]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=2)=[CH:24][C:25]=1[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=[O:35])=[O:34].[CH3:59][C:60]1[N:61]([CH2:87][C:88]([OH:90])=[O:89])[C:62]([C:81]2[CH:82]=[N:83][CH:84]=[CH:85][CH:86]=2)=[CH:63][C:64]=1[CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=1[S:72]([C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)(=[O:73])=[O:74]

Participants

8

Reactant 4

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 67237744HCID 67237744, compoundHCID 67238151HCID 67238151, compound

Product 2

HCID 53246500HCID 53246500, compoundYield 95%HCID 67238151HCID 67238151, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 2-(2-methyl-3-(2-(phenylsulfonyl)benzyl)-5-(pyridin-2-yl)-1H-pyrrol-1-yl)acetate was synthesized according to general procedure I (step 1), with the exception that 6 equivalents of triethylsilane and 4.5 equivalents of trimethylsilyl trifluoromethanesulfonate were used. The crude benzyl 2-(2-methyl-3-(2-(phenylsulfonyl)benzyl)-5-(pyridin-2-yl)-1H-pyrrol-1-yl)acetate was taken forward. In a small recovery flask, H2 was flushed over a stirring solution of benzyl 2-(2-methyl-3-(2-(phenylsulfonyl)benzyl)-5-(pyridin-3-yl)-1H-pyrrol-1-yl)acetate (350 mg, 0.652 mmol), Pd/C (20 mg, 0.019 mmol) in MeOH (2 ml) followed by subjection to 1 atm (balloon) positive pressure of H2. After 1.5 hours, the reaction vial was flushed with nitrogen gas and the mixture was filtered through a 2 micron filter. The colorless mixture was concentrated to afford 2-(2-methyl-3-(2-(phenylsulfonyl)benzyl)-5-(pyridin-3-yl)-1H-pyrrol-1-yl)acetic acid (277 mg, 95%) as a fine yellow powder. 1H NMR (CDCl3/400 MHz) 11.77 (bs, 1H), 8.7 (s, 1H), 8.44 (d, 1H), 8.25 (d, 1H), 7.86-7.82 (m, 3H), 7.54-7.37 (m, 6H), 7.17 (d, 1H), 5.76 (s, 1H), 4.46 (s, 2H), 4.03 (s, 2H), 1.99 (s, 3H). MS m/z=447.4 (M+1).

Workup

  1. customthe reaction
  2. customvial was flushed with nitrogen gas
  3. filtrationthe mixture was filtered through a 2 micron
  4. filtrationfilter
  5. concentrationThe colorless mixture was concentrated

Sources & evidence

ORD record
ord-9f58b6c9e7034fc38a72a7b496e87f3b
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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