Sodium Azide → HCID 59425665, compound

HRID 252554Notes

Reaction equation

HRID 252554 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH2:24][CH3:25])[C:13]3[C:18]([C:19]=2[C:20]#[N:21])=[CH:17][CH:16]=[C:15]([O:22][CH3:23])[CH:14]=3)=[CH:7][CH:6]=1.[N-:26]=[N+:27]=[N-:28].[Na+]>CO>[N:26]([CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH2:24][CH3:25])[C:13]3[C:18]([C:19]=2[C:20]#[N:21])=[CH:17][CH:16]=[C:15]([O:22][CH3:23])[CH:14]=3)=[CH:7][CH:6]=1)=[N+:27]=[N-:28]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 59425563HCID 59425563, compound

Product 1

HCID 59425665HCID 59425665, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

2-[4-(2-Bromoethoxy)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (258 mg, 0.65 mmol), prepared in example 1BA, step A, is combined with NaN3 (144 mg, 2.2 mmol), and MeOH (3.2 mL). This is heated overnight at 75° C. The reaction mixture is then partitioned between CH2Cl2 and H2O. The organic layer is dried and concentrated. Purification by silica gel chromatography (CH2Cl2) yields 2-[4-(2-azidoethoxy)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (187 mg, 80%), compound 266 as a white solid.

Workup

  1. customThe reaction mixture is then partitioned between CH2Cl2 and H2O
  2. customThe organic layer is dried
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-17b1e737f8224aa08d6c2b8c205e5894
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

Loading…