Iodine → 3-iodo-5-(6-isopropoxypyrazin-2-yl)-1H-indole

HRID 1529309Notes

Reaction equation

HRID 1529309 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2].[OH-].[K+].[I:22]I>CN(C=O)C>[I:22][C:14]1[C:13]2[C:17](=[CH:18][CH:19]=[C:11]([C:9]3[CH:8]=[N:7][CH:6]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[N:10]=3)[CH:12]=2)[NH:16][CH:15]=1

Participants

5

Reactant 3

HCID 807Iodine2×HCID 14797Potassium HydroxideHCID 679597185-(6-propan-2-yloxypyrazin-2-yl)-1H-indole

Product 1

HCID 679599583-iodo-5-(6-isopropoxypyrazin-2-yl)-1H-indoleYield 102.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(6-isopropoxy-pyrazin-2-yl)-1H-indole (32 g, 0.126 mol) in DMF (250 mL) was added KOH (17.8 g, 0.316 mol) and then stirred for 15 min at RT. I2 (35.3 g, 0.139 mol) was added to the reaction mixture and stirred at RT for another 1 h. Then reaction mixture was poured into ice water and excess of I2 was quenched with sodium thiosulfite. The resulting solid was collected by filtration, washed with water and dried under vacuum to afford crude 3-iodo-5-(6-isopropoxypyrazin-2-yl)-1H-indole (49 g) as pale brown solid. MS (ESI, m/z): 379.9 (M+1). This material was used to further step without purification.

Workup

  1. stirringstirred at RT for another 1 h
  2. customThen reaction mixture
  3. customwas quenched with sodium thiosulfite
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-548cb172099348ad950af735bdcd369c
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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