HCID 89610367, compound → HCID 71599457, compound

HRID 1507702Notes

Reaction equation

HRID 1507702 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]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:10]=1[C:32]#[N:33])C1C=CC=CC=1>C1COCC1.[Pd]>[OH:8][C:9]1[C:13]([OH:14])=[C:12]([C:22]#[N:23])[N:11]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[C:10]=1[C:32]#[N:33]

Participants

4

Reactant 1

HCID 89610367HCID 89610367, compound

Product 1

HCID 71599457HCID 71599457, compoundYield 14.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3,4-Bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarbonitrile (14) (70 mg, 0.16 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 25° C. under H2 (full H2 mode). The output was concentrated in vacuo to afford the crude product. The compound was purified by preparative HPLC (C-18 column, 21.2 mm i.d.×100 mm, 5 micron particle size, gradient 5-95% MeCN in 0.1% aqueous formic acid over 16 min) to afford 3,4-dihydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarbonitrile (UL1-034) (6 mg, 14%) as a yellow powder: m/z 254 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 7.44-7.36 (m, 2H), 7.14-7.05 (m, 2H).

Workup

  1. customat 25° C.
  2. concentrationThe output was concentrated in vacuo
  3. customto afford the crude product
  4. customThe compound was purified by preparative HPLC (C-18 column, 21.2 mm i.d.×100 mm, 5 micron particle size, gradient 5-95% MeCN in 0.1% aqueous formic acid over 16 min)

Sources & evidence

ORD record
ord-1c77b85615bf4c7daba6372e7b1321b7
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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