Tetrahydrofuran → HCID 58547973, compound

HRID 2207815Notes

Reaction equation

HRID 2207815 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[C:23]([N:24]3[CH2:29][CH2:28][CH:27]([C:30]#N)[CH2:26][CH2:25]3)=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:13][CH2:12]1.CC(C[AlH]CC(C)C)C.C1C[O:44]CC1>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[C:23]([N:24]3[CH2:29][CH2:28][CH:27]([CH:30]=[O:44])[CH2:26][CH2:25]3)=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 58547825HCID 58547825, compound

Product 1

HCID 58547973HCID 58547973, compoundYield 80%

Procedure

To a solution of 1-(2-((1-(quinolin-2-yl)piperidin-4-yl)oxy)pyridin-3-yl)piperidine-4-carbonitrile (290 mg, 0.70 mol) in 20 mL of THF was added DIBAL-H (1.4 mol, 1 M in toluene) dropwise at −65° C. The mixture was stirred for 1 hour at RT and then quenched with saturated aqueous NH4Cl. The resulting mixture was extracted with EtOAc (2×20 mL) and the combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give the product (0.232 g, 0.56 mmol, 80% yield). ESI-MS (M+1): 417 calc. for C25H28N4O2 416.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionThe resulting mixture was extracted with EtOAc (2×20 mL)
  3. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6f5b26f10a814a8793bf3ded4f1c7ab9
Source dataset
uspto-grants-2016_06
Patent number
US09376450B2

Reaction notes

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