Pyrrole → HCID 11188835, compound

HRID 1883471Notes

Reaction equation

HRID 1883471 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:13])[CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1)=[O:4].N1C=CC=C1.[F:19][C:20]([F:44])([F:43])[C:21]1[CH:26]=[CH:25][C:24]([S:27][CH2:28][CH2:29][O:30][C:31](=O)[O:32]C2C=CC([N+]([O-])=O)=CC=2)=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1>CC(=O)OCC.C(Cl)Cl.CN(C1C=CN=CC=1)C.[Pd].O>[CH3:13][N:6]1[CH:7]=[C:8]([NH:10][C:31]([O:30][CH2:29][CH2:28][S:27][C:24]2[CH:25]=[CH:26][C:21]([C:20]([F:19])([F:44])[F:43])=[CH:22][CH:23]=2)=[O:32])[CH:9]=[C:5]1[C:3]([O:2][CH3:1])=[O:4]

Participants

11

Reactant 5

HCID 8027PyrroleHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2759930Methyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylateHCID 11165106HCID 11165106, compound

Product 1

HCID 11188835HCID 11188835, compoundYield 85.42%

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23938PalladiumCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After 1-methyl-4-nitropyrrole-2-carboxylic acid methyl ester (1.17 g, 6.35 mmol) was dissolved in EA (20 ml), 10% Pd/C (50 mg, catalytic weight) was added thereto. The mixture was stirred for 1 hour at room temperature under hydrogen atmosphere to reduce a nitro group (NO2) into an amino group (NH2), whereby a pyrrole-type amino acid was obtained. 10% Pd/C was filtered out by celite 545 filter, and the filtrate was washed with EA and MeOH and concentrated under vacuum. To the residue were added carbonic acid 4-nitro-phenyl ester 2-(4-trifluoromethyl-phenylsulfanyl)-ethyl ester (2.23 g, 5.76 mmol) dissolved in anhydrous DCM (30 ml), DIEA (2.01 μm, 11.56 mmol), DMAP (1.41 g, 11.56 mmol), and HOBt (1.77 g, 11.56 mmol), and the mixture was stirred for 12 hours at room temperature. The reaction was stopped by adding water and the reaction mixture was extracted with DCM. The organic layer was dried over anhydrous MgSO4 and concentrated. The residue was purified by silica gel column chromatography (EA/n-hexane=1/3, v/v) to give methyl 1-methyl-4-[2-(4-trifluoromethyl-phenylsulfanyl)-ethoxycarbonylamino]-1H-pyrrole-2-carboxylate (1.98 g, 85.42%) of a pale yellow solid.

Workup

  1. customwas obtained
  2. filtration10% Pd/C was filtered out by celite 545
  3. filtrationfilter
  4. washthe filtrate was washed with EA and MeOH
  5. concentrationconcentrated under vacuum
  6. extractionthe reaction mixture was extracted with DCM
  7. dry with materialThe organic layer was dried over anhydrous MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (EA/n-hexane=1/3

Sources & evidence

ORD record
ord-9ec5679d050247aaafdbd1d23056dd5e
Source dataset
uspto-grants-2004_07
Patent number
US06759511B2

Reaction notes

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