Sodium hydride → HCID 67044267, compound

HRID 2367100Notes

Reaction equation

HRID 2367100 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2.[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14]>CN(C)C=O.C(OCC)(=O)C.O>[I:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:13]([CH3:15])[CH3:14])[N:8]=[CH:7]2

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 218947395-Iodo-1H-indazole

Product 1

HCID 67044267HCID 67044267, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of sodium hydride (0.67 g, 17 mmol) in N,N-dimethylformamide (43 mL) cooled to 0° C. was added 5-iodo-1H-indazole (3.1 g, 13 mmol). After stirring for 15 min, triisopropylsilyl chloride (3.4 mL, 17 mmol) was added dropwise and the solution was allowed to warm to room temperature. The solution was diluted with ethyl acetate and water and the layers were separated. The aqueous layer was extracted (2×100 mL ethyl acetate) and the combined organic layers were dried (sodium sulfate), filtered and concentrated in vacuo. Column chromatography (silica gel, 20:1 hexanes/ethyl acetate) gave 1.8 g (68%) of 5-iodo-1-[tris(1-methylethyl)silyl]-1H-indazole as a yellow solid. 1H NMR (400 MHz, CDCl3): 8.14 (d, 1H), 8.11 (d, 1H), 7.55 (dd, 1H), 7.35 (d, 1H), 1.77 (m, 3H), 1.10 (m, 18H).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted (2×100 mL ethyl acetate)
  3. dry with materialthe combined organic layers were dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8f87ea4cea64f9aab8257680d23207d
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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