Hydrochloric Acid → HCID 59146184, compound

HRID 1512794Notes

Reaction equation

HRID 1512794 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24]([CH3:26])[CH:23]=[C:22]4/[CH:27]=[CH:28]/[O:29]C)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Cl>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24]([CH3:26])[CH:23]=[C:22]4[CH2:27][CH:28]=[O:29])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59146072HCID 59146072, compound

Product 1

HCID 59146184HCID 59146184, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-3-[(E)-2-(methyloxy)ethenyl]-1H-indole (D61) (1.2 g) in 1,4-dioxane (20 mL) stirred was added a solution of HCl (20 mL) in water. The reaction mixture was stirred at 20° C. for 30 mins. The reaction mixture was quenched with NaHCO3, partitioned between ethyl acetate (100 mL) and water (50 mL). The organic phase was washed with water and brine, dried over sodium sulphate and evaporated to give the crude product as a brown oil, which was purified by Mass Directed Auto Prep (basic) to afford [7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]acetaldehyde (D88) (220 mg) as a white solid. δH (CDCl3, 400 MHz): 1.39 (6H, d), 3.70 (3H, s), 3.77 (2H, d), 4.66 (1H, m), 7.00 (2H, m), 7.17 (1H, t), 7.53 (1H, dd), 7.62 (1H, dd), 8.01 (1H, dd), 8.19 (1H, dd), 9.70 (1H, t). MS (ES): C22H20ClN3O3 requires 409. found 410.2 (M+H+).

Workup

  1. customThe reaction mixture was quenched with NaHCO3
  2. custompartitioned between ethyl acetate (100 mL) and water (50 mL)
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto give the crude product as a brown oil, which
  7. customwas purified by Mass Directed Auto Prep (basic)

Sources & evidence

ORD record
ord-a78a9d84c25949f6bf215b0017bd792f
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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