Isobutyraldehyde → HCID 57510045, compound

HRID 624176Notes

Reaction equation

HRID 624176 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([N:16]3[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)=[O:15])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH:25](=O)[CH:26]([CH3:28])[CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH2:25]([N:1]1[CH2:2][CH:3]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([N:16]3[CH2:17][C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:24]3)=[O:15])=[CH:9][CH:8]=2)[CH2:5][CH2:6]1)[CH:26]([CH3:28])[CH3:27]

Participants

8

Reactant 3

HCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57509942HCID 57509942, compound

Product 1

HCID 57510045HCID 57510045, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

In a 4 mL were mixed N-(4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)isoindoline-2-carboxamide (50 mg, 0.157 mmol) and isobutyraldehyde (0.014 ml, 0.157 mmol) in anhydrous dichloroethane (2 ml) at room temperature. Sodium triacetoxyborohydride (46.4 mg, 0.219 mmol) was added, and reaction was stirred overnight. The reaction mixture was diluted with water, ethyl acetate and saturated aqueous sodium bicarbonate. The layers were separated and the organic layer was washed with brine. The organic layer was diluted with methanol, dried with sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.35 (s, 1H), 7.53-7.55 (m, 2H), 7.30-7.38 (m, 6H), 6.06-6.08 (m, 1H), 4.77 (s, 4H), 3.01-3.03 (m, 2H), 2.57 (t, J=5.6 Hz, 2H), 2.41-2.47 (m, 2H), 2.14 (d, J=7.3 Hz, 2H), 1.77-1.88 (m, 1H), 0.88 (d, J=6.5 Hz, 6H); MS (ESI(−)) m/e 374 (M−H)−.

Workup

  1. customreaction
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. additionThe organic layer was diluted with methanol
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-558ea4d9b055444f87d18fe4c101e2a5
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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