Toluene → HCID 86676172, compound

HRID 55882Notes

Reaction equation

HRID 55882 reaction equation
[CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9]1[CH:10]=[CH:11][C:12]([C:15]#N)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C1C[O:43]CC1>>[CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:43])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 666069135-(Dibenzylamino)picolinonitrile

Product 1

HCID 86676172HCID 86676172, compoundYield 69%

Procedure

To a solution of 38 (500 mg, 1.7 mmol) in THF (25 mL) was added 1.6M DIBALH in toluene (3.1 mL, 5.01 mmol) at −78° C. and stirred for 3 h at the same temperature. The reaction mixture was quenched with water (20 mL), extracted with EtOAc (2×50 mL), the combined organic layers were washed with brine (20 mL), dried (Na2SO4) and evaporated. The crude compound was purified by silica gel column chromatography (100-200 mesh, eluted with 20% EtOAc/pet-ether) to obtain compound 39 (350 mg, 69%) as a brown solid. Rf: 0.5 (40% EtOAc/pet-ether); (m/z): 303 [MH]+; 1H NMR (400 MHz, CDCl3): δ 9.85 (1H, S), 8.27 (1H, d, J=2.8 Hz), 7.79 (1H, d, J=8.8 Hz), 7.38-7.20 (10H, m), 7.03 (1H, dd, J=3.2, 8.8 Hz), δ 4.77 (4H, s).

Workup

  1. customThe reaction mixture was quenched with water (20 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. washthe combined organic layers were washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude compound was purified by silica gel column chromatography (100-200 mesh, eluted with 20% EtOAc/pet-ether)

Sources & evidence

ORD record
ord-0b5e0fb7b1544828957ba04af4fc1dca
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

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