Iodine → HCID 178519291, compound

HRID 2078735Notes

Reaction equation

HRID 2078735 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]([CH2:9][OH:10])[S:8][C:4]=2[CH:3]=[N:2]1.[OH-].[K+].[I:13]I.S(=O)(O)[O-].[Na+]>CN(C)C=O.O>[I:13][C:3]1[C:4]2[S:8][C:7]([CH2:9][OH:10])=[CH:6][C:5]=2[NH:1][N:2]=1

Participants

7

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 23665763Sodium BisulfiteHCID 57354336(1H-Thieno[3,2-c]pyrazol-5-yl)methanol2×

Product 1

HCID 178519291HCID 178519291, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (1H-thieno[3,2-c]pyrazol-5-yl)-methanol [3.2 g, 20.8 mmol, Intermediate (70)] in solution in dimethyl formamide (40 mL) were added potassium hydroxide (3.5 g, 62.3 mmol) and iodine (7.9 g, 31.1 mmol). The mixture was stirred at room temperature for 5 hours. A concentrated solution of sodium bisulfite in water was added until the orange color disappeared. The resulting mixture was extracted several times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated. The residue was triturated in dichloromethane to produce (3-iodo-1H-thieno[3,2-c]pyrazol-5-yl)-methanol [5.3 g, 91%, Intermediate (71)]. LC/MS: 280.91 (M+H), RT=1.93 minutes; 1H NMR [300 Mhz, (CD3)2SO]: δ13.23 (s, 1H), 7.12 (s, 1H), 5.64 (t, J=6.6 Hz, 1H), 4.63 (d, J=6.5 Hz, 1H).

Workup

  1. extractionThe resulting mixture was extracted several times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was triturated in dichloromethane

Sources & evidence

ORD record
ord-e05bbc791edc4245abb6d8f3653dc6c3
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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