N-Iodosuccinimide → HCID 89610330, compound

HRID 1507722Notes

Reaction equation

HRID 1507722 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C:17]1[C:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][N:19]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:18]=1[C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OC1C(OCC2C=CC=CC=2)=C(C(OCC)=O)N(C2C=CC(OC)=CC=2)C=1C([O-])=O)C1C=CC=CC=1.C([NH+](CC)CC)C>CN(C=O)C>[CH2:9]([O:16][C:17]1[C:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:20]([I:1])[N:19]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:18]=1[C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 89610435HCID 89610435, compoundHCID 89610545HCID 89610545, compound

Product 1

HCID 89610330HCID 89610330, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

N-Iodosuccinimide (1.77 g, 7.57 mmol) was added to a solution of ethyl 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (27) [prepared using the same procedure as Example E step (i) using (5) as starting material] (3.0 g, 6.56 mmol) in DMF (60 mL) and stirred at 0° C. for 10 min. The mixture was partitioned between sat. Na2S2O3 (aq.) (100 mL) and Et2O (250 mL), the organic layer was separated and washed with sat. Na2S2O3 (aq.) (100 mL), brine (100 mL) dried (MgSO4), filtered and solvents removed in vacuo. The crude residue was purified by silica gel chromatography (120 g, 0-40% Et2O in isohexane) to afford ethyl 3,4-bis(benzyloxy)-5-iodo-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (28) (2.92 g, 76%) as a white solid: m/z 584 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.51-7.29 (m, 10 H), 7.14-7.05 (m, 2H), 7.03-6.92 (m, 2H), 5.12 (s, 2H), 5.00 (s, 2H), 3.97 (q, J=7.1 Hz, 2H) 3.82 (s, 3H), 0.99 (t, J=7.1 Hz, 3H).

Workup

  1. customprepared
  2. customThe mixture was partitioned between sat. Na2S2O3 (aq.) (100 mL) and Et2O (250 mL)
  3. customthe organic layer was separated
  4. washwashed with sat. Na2S2O3 (aq.) (100 mL), brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customsolvents removed in vacuo
  8. customThe crude residue was purified by silica gel chromatography (120 g, 0-40% Et2O in isohexane)

Sources & evidence

ORD record
ord-49a65d04a4924402924ba8ec4d0616d6
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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