Potassium Iodide → HCID 117642481, compound

HRID 1507740Notes

Reaction equation

HRID 1507740 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][N:10]([CH3:33])[C:11]([C:13]1[N:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:16]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:15]([OH:31])[C:14]=1[OH:32])=[O:12].[I-].[K+].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH2:1]([O:31][C:15]1[C:14]([OH:32])=[C:13]([C:11](=[O:12])[N:10]([CH3:33])[CH3:9])[N:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:16]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 71576576HCID 71576576, compound

Product 1

HCID 117642481HCID 117642481, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Benzyl bromide (3.94 mL, 33.2 mmol) was added to a stirred suspension of ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (UL1-012) (10.5 g, 30.1 mmol), potassium iodide (5.50 g, 33.2 mmol) and K2CO3 (4.58 g, 33.2 mmol) in DMF (100 mL). The reaction was allowed to stir at 80° C. for 24 h. The reaction mixture was poured into water (200 mL), washed with Et2O (2×200 mL), and the combined organic layers were washed with 1M HCl (aq.) (400 mL), brine (2×400 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (330 g, 0-50% EtOAc in toluene) to afford ethyl 3-(benzyloxy)-5-(dimethylcarbamoyl)-4-hydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (41) (4.36 g, 33%) as a pale yellow solid: m/z 439 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 8.82 (s, 1H), 7.53-7.47 (m, 2H), 7.42-7.29 (m, 3H), 7.08-7.01 (m, 2H), 6.90-6.84 (m, 2H), 5.09 (s, 2H), 3.96 (q, J=7.0 Hz, 2H), 3.76 (s, 3H), 2.82 (br s, 6H), 0.97 (t, J=7.0 Hz, 3H).

Workup

  1. washwashed with Et2O (2×200 mL)
  2. washthe combined organic layers were washed with 1M HCl (aq.) (400 mL), brine (2×400 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography (330 g, 0-50% EtOAc in toluene)

Sources & evidence

ORD record
ord-af1579752e894a0a9982000d56aa200b
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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