Aniline → HCID 56926180, compound

HRID 2175463Notes

Reaction equation

HRID 2175463 reaction equation
[CH3:1][C:2]1([CH3:14])[O:11][C:10]2[C:5](=[N:6][C:7]([CH:12]=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH3-]C#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:1][C:2]1([CH3:14])[O:11][C:10]2[C:5](=[N:6][C:7]([CH2:12][NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Participants

6

Reactant 3

HCID 6115AnilineHCID 5003444Sodium cyanoborohydrideHCID 56925649HCID 56925649, compound

Product 1

HCID 56926180HCID 56926180, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2,2-dimethyl-2H-pyrano[3,2-b]pyridine-6-carbaldehyde (434 mg, 2.28 mmol) in methanol (3 mL) was added aniline (0.3 mL, 2.52 mmol) and zinc chloride (621 mg, 4.56 mmol) and stirred at room temperature for 2 hours. Then NaCNBH3 (287 mg, 4.56 mmol) was added and stirred overnight. Purification by column: 4:1 Hx/EtOAc to give an off-white solid. Yield: 48%. 1H NMR (CDCl3) δ 1.49 (s, 6H), 4.361 (s, 2H), 5.91 (d, 1H, J=10), 6.55 (d, 1H, J=10), 6.68-6.71 (m, 3H), 7.01 (d, 1H, J=8.4), 7.08 (d, 1H, J=8.4), 7.18-7.38 ppm (m, 2H).

Workup

  1. stirringstirred overnight
  2. customPurification by column
  3. custom4:1 Hx/EtOAc to give an off-white solid

Sources & evidence

ORD record
ord-968476def1854baf9a644ac21c547ab1
Source dataset
uspto-grants-2015_06
Patent number
US09062072B2

Reaction notes

Loading…