HCID 71599882, compound → HCID 71599543, compound

HRID 1507704Notes

Reaction equation

HRID 1507704 reaction equation
C([O:8][C:9]1[C:13]([O:14]CC2C=CC=CC=2)=[C:12]([C:22]#[N:23])[N:11]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[C:10]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32])C1C=CC=CC=1>C1COCC1.[Pd]>[C:22]([C:12]1[N:11]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[C:10]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:9]([OH:8])[C:13]=1[OH:14])#[N:23]

Participants

4

Reactant 1

HCID 71599882HCID 71599882, compound

Product 1

HCID 71599543HCID 71599543, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3,4-bis(benzyloxy)-5-cyano-1-(4-fluorophenyl)-1H-pyrrole-2-carboxylate (UL1-060) (102 mg, 0.22 mmol) in THF (5 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1.5 mL/min at 20° C. under H2 (full H2 mode). The output was concentrated in vacuo to afford the crude product. The crude residue was purified by silica gel chromatography (4 g, 0-35% EtOAc in isohexane) to afford ethyl 5-cyano-1-(4-fluorophenyl)-3,4-dihydroxy-1H-pyrrole-2-carboxylate (UL1-039) (18 mg, 29% yield) as a white solid: m/z 291 (M+H)+ (ES+); 289 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 10.14 (s, 1H), 8.99 (s, 1H), 7.44-7.36 (m, 2H), 7.35-7.26 (m, 2H), 4.05 (q, J=7.1 Hz, 2H), 1.01 (t, J=7.1 Hz, 3H).

Workup

  1. customat 20° C.
  2. concentrationThe output was concentrated in vacuo
  3. customto afford the crude product
  4. customThe crude residue was purified by silica gel chromatography (4 g, 0-35% EtOAc in isohexane)

Sources & evidence

ORD record
ord-642623f871ec426688ec4e30ce53cfd8
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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