Hydrochloric Acid → HCID 59425830, compound

HRID 502181Notes

Reaction equation

HRID 502181 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 EL). 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-58e5558eba6444fcabf6c2db615684ca
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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