Hydrochloric Acid → HCID 59425830, compound

HRID 907163Notes

Reaction equation

HRID 907163 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH2:26][CH3:27])[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24][CH3:25])[CH:16]=3)=[CH:9][CH:8]=1)=[N+]=[N-].Cl>[Pd].CO>[NH2:1][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH2:26][CH3:27])[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24][CH3:25])[CH:16]=3)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59425665HCID 59425665, compound

Product 1

HCID 59425830HCID 59425830, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-[4-(2-Azidoethoxy)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (410 mg, 1.14 mmol), prepared as in step A, above, was suspended in a solution of MeOH (20 mL) and concentrated HCl (500 μL). Pd/C (150 mg, 10%) was added, and this mixture was hydrogenated at 30 p.s.i. for 1 h. This was filtered and the filtrate was concentrated. The filtrate residue was partitioned between EtOAc and 0.5N NaOH. The organic layer was dried and concentrated. Purification by silica gel chromatography (10-30%, MeOH/CH2Cl2) yielded 2-[4-(2-aminoethoxy)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (298 mg, 78%), compound 267, as a white solid.

Workup

  1. filtrationThis was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe filtrate residue was partitioned between EtOAc and 0.5N NaOH
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (10-30%, MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8c33920781984ed0a10590aea111bdbb
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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