Hydrochloric Acid → HCID 59425830, compound

HRID 506063Notes

Reaction equation

HRID 506063 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, is suspended in a solution of MeOH (20 mL) and concentrated HCl (500 μL). Pd/C (150 mg, 10%) is added, and this mixture is hydrogenated at 30 p.s.i. for 1 h. This is filtered and the filtrate is concentrated. The filtrate residue is partitioned between EtOAc and 0.5N NaOH. The organic layer is dried and concentrated. Purification by silica gel chromatography (10-30%, MeOH/CH2Cl2) yields 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 is filtered
  2. concentrationthe filtrate is concentrated
  3. customThe filtrate residue is partitioned between EtOAc and 0.5N NaOH
  4. customThe organic layer is dried
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (10-30%, MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-de87b7f41ee041f184eae3ea3f5bb6a6
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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