Lithium Hexamethyldisilazide → HCID 86699352, compound

HRID 706745Notes

Reaction equation

HRID 706745 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:11][C:12]1[N:17]=[C:16]([CH2:18][N:19]2[C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([NH2:28])[C:22]=3[CH:21]=[N:20]2)[CH:15]=[CH:14][CH:13]=1.[CH3:29][N:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][O:38][C:39]2[CH:44]=[CH:43][N:42]3[C:45]([C:48](OCC)=[O:49])=[CH:46][N:47]=[C:41]3[CH:40]=2)[CH2:32][CH2:31]1>C1COCC1.C([O-])(O)=O.[Na+]>[CH3:29][N:30]1[CH2:31][CH2:32][N:33]([CH2:36][CH2:37][O:38][C:39]2[CH:44]=[CH:43][N:42]3[C:45]([C:48]([NH:28][C:23]4[CH:24]=[CH:25][CH:26]=[C:27]5[C:22]=4[CH:21]=[N:20][N:19]5[CH2:18][C:16]4[CH:15]=[CH:14][CH:13]=[C:12]([CH3:11])[N:17]=4)=[O:49])=[CH:46][N:47]=[C:41]3[CH:40]=2)[CH2:34][CH2:35]1

Participants

6

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 67254998Ethyl 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylateHCID 67976246HCID 67976246, compound

Product 1

HCID 86699352HCID 86699352, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

LHMDS (1.595 mL, 1.595 mmol, 1.0M THF) was added drop-wise to a solution of 1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (0.190 g, 0.7974 mmol) in THF (4 mL) at 0° C., resulting in a dark solution. The mixture was stirred at 0° C. for 10 minutes, then ethyl 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate (Preparation A; 0.5566 g, 1.674 mmol) was added in one portion and the mixture was stirred overnight. The reaction mixture was diluted with saturated aqueous NaHCO3 and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (5 to 20% MeOH/CH2Cl2 using 5% NH4OH/MeOH) to provide 0.254 g (61%) of the desired product as a pale brown powder. MS (ES+APCI) m/z=525 (M+H).

Workup

  1. customresulting in a dark solution
  2. addition0.5566 g, 1.674 mmol) was added in one portion
  3. stirringthe mixture was stirred overnight
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (5 to 20% MeOH/CH2Cl2 using 5% NH4OH/MeOH)

Sources & evidence

ORD record
ord-01138b3ed5f14a1a85e49e1a67a2dfdf
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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