Imidazole → HCID 178460605, compound

HRID 246318Notes

Reaction equation

HRID 246318 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[C:6]([C:11]([OH:14])([CH3:13])[CH3:12])[CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.N1C=CN=C1.[CH3:20][Si:21](Cl)([CH3:23])[CH3:22]>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[C:6]([C:11]([CH3:12])([O:14][Si:21]([CH3:23])([CH3:22])[CH3:20])[CH3:13])[CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 178458234HCID 178458234, compound

Product 1

HCID 178460605HCID 178460605, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round-bottomed flask, 2-(3-iodo-1H-indazol-7-yl)-propan-2-ol (crude from Step 2, 479 mg, 1.11 mmol) was dissolved in DMF (3.2 ml) and imidazole (189 mg, 2.77 mmol) and trimethylsilyl chloride (0.17 ml, 1.33 mmol) were added. The reaction mixture was stirred at room temperature overnight then quenched with water and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated to give 383 mg (88%) of 3-iodo-7-(1-methyl-1-trimethylsilanyloxy-ethyl)-1H-indazole as a light yellow solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 10.86 (br. s., 1H), 7.40 (dd, J=6.8, 2.3 Hz, 1H), 7.12-7.21 (m, 2H), 1.73 (s, 6H), 0.11 (s, 9H).

Workup

  1. customthen quenched with water
  2. extractionextracted with diethyl ether (2×)
  3. washThe combined organic layers were washed twice with water and once with brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8771230162424901a983eb1082352f78
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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