HCID 89610332, compound → HCID 136252909, compound

HRID 1507726Notes

Reaction equation

HRID 1507726 reaction equation
C([O:8][C:9]1[C:13]([O:14]CC2C=CC=CC=2)=[C:12]([C:22]2[S:23][CH:24]=[C:25]([CH2:27][CH3:28])[N:26]=2)[N:11]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C:10]=1[C:37]([O:39][CH2:40][CH3:41])=[O:38])C1C=CC=CC=1>CO.C1COCC1.[Pd]>[CH2:27]([C:25]1[N:26]=[C:22]([C:12]2[N:11]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[C:10]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[C:9]([OH:8])[C:13]=2[OH:14])[S:23][CH:24]=1)[CH3:28]

Participants

4

Reactant 1

HCID 89610332HCID 89610332, compound

Product 1

HCID 136252909HCID 136252909, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of ethyl 3,4-bis(benzyloxy)-5-(4-ethylthiazol-2-yl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (30) (70 mg, 0.12 mmol) in MeOH/THF (3:1; 5 mL) was passed through a Thales ‘H-cube’ cartridge (10 Pd/C) at a flow rate of 1 mL/min at 40° C. under H2 (full H2 mode). The output was concentrated in vacuo and the resulting oil was purified by silica gel chromatography (12 g, 0-20% EtOAc in isohexane) to afford ethyl 5-(4-ethylthiazol-2-yl)-3,4-dihydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (UL1-086) (30 mg, 63%) as an off-white solid: m/z 389 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 1H NMR (400 MHz, DMSO-d6) δ: 9.82 (s, 1H), 8.68 (s, 1H), 7.28-7.19 (m, 2H), 7.06-7.03 (m, 1H), 7.03-6.97 (m, 2H), 4.00 (q, J=7.1 Hz, 2H), 3.82 (s, 3H), 2.67 (q, J=7.5 Hz, 2H), 1.16 (t, J=7.5 Hz, 3H), 0.99 (t, J=7.1 Hz, 3H).

Workup

  1. customat 40° C.
  2. concentrationThe output was concentrated in vacuo
  3. customthe resulting oil was purified by silica gel chromatography (12 g, 0-20% EtOAc in isohexane)

Sources & evidence

ORD record
ord-64d9eddabc8f41a08a7f34efaa451cdb
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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