Pyridine → HCID 66779688, compound

HRID 1470386Notes

Reaction equation

HRID 1470386 reaction equation
[O:1]([C:8]1[CH:30]=[CH:29][C:11]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[CH:19]=[C:20]([C:22]4[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=4)[NH2:25])[O:21][C:14]=23)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:37](Cl)(=[O:40])[CH2:38][CH3:39]>O>[O:1]([C:8]1[CH:30]=[CH:29][C:11]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[CH:19]=[C:20]([C:22]4[CH:23]=[C:24]([NH:25][C:37](=[O:40])[CH2:38][CH3:39])[CH:26]=[CH:27][CH:28]=4)[O:21][C:14]=23)=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 56848930HCID 56848930, compound

Product 1

HCID 66779688HCID 66779688, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 20-mL glass vial was added 3-[7-(4-phenoxyphenoxy)furo[3,2-b]pyridin-2-yl]aniline (30.00 mg; 0.08 mmol) and pyridine (1.00 ml). The resulting mixture was cooled to 0° C. and stirred for 5 minutes. Then propanoyl chloride (0.01 ml; 0.08 mmol) was added. The ice bath was left to melt. The reaction mixture was stirred at room temperature overnight. Water was added to the mixture which was then extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude mixture was purified using Biotage column chromatography (50-100% EtOAc/Hexanes) to afford the title compound as a white solid (28.00 mg, 82%). HPLC (method F): 92%, RT=4.530 min. 1H NMR (DMSO-d6) δ [ppm] 7.52 (d, 1H), 7.45 (d, 1H), 6.85-6.80 (dd, 2H), 6.70-6.64 (q, 1H), 6.60-6.49 (m, 6H), 6.36-6.34 (m, 3H), 6.26 (d, 2H), 6.01 (d, 1H), 1.63 (q, 2H), 0.42 (t, 3H). MS: m/z=451 [M+H]+, RT=4.08 min.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. extractionwas then extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude mixture was purified

Sources & evidence

ORD record
ord-258af5b491b046f3b8355fd382e98e26
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

Loading…