Iodine → HCID 178489659, compound

HRID 2078727Notes

Reaction equation

HRID 2078727 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:11]2[S:18][C:17]3[CH:16]=[N:15][NH:14][C:13]=3[CH:12]=2)[CH:8]=[CH:9][CH:10]=1.[I:19]I>CN(C)C=O>[I:19][C:16]1[C:17]2[S:18][C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH3:3])[CH:6]=3)=[CH:12][C:13]=2[NH:14][N:15]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 57637387HCID 57637387, compound2×

Product 1

HCID 178489659HCID 178489659, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crushed potassium hydroxide (1.35 g, 24.1 mmol) was added in one portion to a solution of 5-(3-methoxyphenyl)-1H-thieno[3,2-c]pyrazole [1.85 g, 8.03 mmol, Intermediate (53)] and dimethylformamide at 0° C. with stirring. After 10 minutes, iodine (3.05 g, 12.0 mmol) was added in one portion and the dark reaction was stirred at 0° C. for 30 minutes and then at room temperature for 5 hours. The reaction was quenched with 10% aqueous NaHSO3 (100 mL), the resulting white mixture diluted with water (100 ml) and the mixture aged at 5° C. overnight. The solid was collected by filtration, washed with water (3×30 mL) and dried under vacuum at 40° C. to give 3-iodo-5-(3-methoxyphenyl)-1H-thieno[3,2-c]pyrazole [2.61 g, 91%, Intermediate (54)] as a tan powder. mp 159-163° C.; TLC Rf 0.54 (silica, 80% ethyl acetate/heptane); LC/MS: 357.0 (M+H), RT=3.60 minutes; 1H NMR (300 Mhz, CDCl3) δ 11.3 (br s, 1H), 7.33 (m, 1H), 7.28-7.20 (m, 2H), 7.14 (m, 1H), 6.91 (m, 1H), 3.87 (s, 3H).

Workup

  1. customthe dark reaction
  2. stirringwas stirred at 0° C. for 30 minutes
  3. waitat room temperature for 5 hours
  4. customThe reaction was quenched with 10% aqueous NaHSO3 (100 mL)
  5. additionthe resulting white mixture diluted with water (100 ml)
  6. waitthe mixture aged at 5° C. overnight
  7. filtrationThe solid was collected by filtration
  8. washwashed with water (3×30 mL)
  9. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-47874d512b864c1d8a163822cdb74cb0
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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