HCID 71598746, compound → HCID 136252908, compound

HRID 1507724Notes

Reaction equation

HRID 1507724 reaction equation
C([O:8][C:9]1[C:13]([O:14]CC2C=CC=CC=2)=[C:12]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[N:11]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[C:10]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37])C1C=CC=CC=1>CO.C1COCC1.[Pd]>[OH:8][C:9]1[C:13]([OH:14])=[C:12]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[N:11]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[C:10]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37]

Participants

4

Reactant 1

HCID 71598746HCID 71598746, compound

Product 1

HCID 136252908HCID 136252908, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of ethyl 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-5-(pyridin-2-yl)-1H-pyrrole-2-carboxylate (UL1-082) (146 mg, 0.273 mmol) in MeOH/THF (9:1; 20 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 30° C. under H2 (full H2 mode). The output was concentrated in vacuo and the resulting oil was purified by silica gel chromatography (12 g, 0-2% MeOH in DCM) to afford ethyl 3,4-dihydroxy-1-(4-methoxyphenyl)-5-(pyridin-2-yl)-1H-pyrrole-2-carboxylate (UL1-083) (86 mg, 89%) as a pale orange solid: m/z 355 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 10.84 (s, 1H), 8.62 (s, 1H), 8.56-8.47 (m, 1H), 7.67-7.55 (m, 1H), 7.26-7.12 (m, 3H), 7.01-6.89 (m, 2H), 6.62-6.49 (m, 1H), 4.01 (q, J=7.1 Hz, 2H), 3.80 (s, 3H), 1.02 (t, J=7.1 Hz, 3H).

Workup

  1. customat 30° C.
  2. concentrationThe output was concentrated in vacuo
  3. customthe resulting oil was purified by silica gel chromatography (12 g, 0-2% MeOH in DCM)

Sources & evidence

ORD record
ord-c880abd706524a308dab4981ecf9255d
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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