3-Iodo-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine → HCID 66970896, compound

HRID 1754785Notes

Reaction equation

HRID 1754785 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:3]=1.C([Mg]Cl)(C)C.C(OC(=O)[N:32]([C:44]1[CH:49]=[CH:48][C:47]([C:50](=[O:52])[CH3:51])=[CH:46][N:45]=1)[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=1)(C)(C)C>O1CCCC1>[F:43][C:40]([F:41])([F:42])[C:37]1[CH:38]=[CH:39][C:34]([CH2:33][NH:32][C:44]2[N:45]=[CH:46][C:47]([C:50]([C:2]3[C:10]4[C:5](=[N:6][CH:7]=[CH:8][CH:9]=4)[N:4]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:3]=3)([OH:52])[CH3:51])=[CH:48][CH:49]=2)=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 242292273-Iodo-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridineHCID 57619361HCID 57619361, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 66970896HCID 66970896, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-20 °C

Procedure

3-Iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (96, 485.9 mg, 1.21 mmol) was dissolved in tetrahydrofuran (8 mL) at −20° C. under an atmosphere of nitrogen. 2.0 M isopropylmagnesium chloride in tetrahydrofuran (0.655 mL) was added. The reaction was stirred at −20° C. for 1 hour. Into the reaction was added (5-acetyl-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester (621, 300.0 mg, 0.76 mmol) in tetrahydrofuran (6 mL) The reaction was allowed to warm to room temperature overnight. The mixture was extracted with ethyl acetate and saturated sodium bicarbonate. The organic portions were dried with anhydrous sodium sulfate, filtered and the filtrate was adsorbed onto silica. The mixture was purified by silica gel chromatography on the (ethyl acetate:hexanes), to provide the desired compound as an oil (622, 125 mg, 29%), consistent with the compound structure by 1H-NMR.

Workup

  1. temperatureto warm to room temperature overnight
  2. extractionThe mixture was extracted with ethyl acetate and saturated sodium bicarbonate
  3. dry with materialThe organic portions were dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe mixture was purified by silica gel chromatography on the (ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-efde68fe6ed34c18a4701066ad732034
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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