Dichloromethane → 4-Azido-5,6,7,8-tetrahydro-7-(phenylmethyl)-1,7-naphthyridine

HRID 1593599Notes

Reaction equation

HRID 1593599 reaction equation
[CH2:1]([N:8]1[CH2:17][C:16]2[N:15]=[CH:14][CH:13]=[C:12](Cl)[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:19]=[N+:20]=[N-:21].[Na+].C(Cl)Cl>CN(C=O)C>[N:19]([C:12]1[C:11]2[CH2:10][CH2:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:17][C:16]=2[N:15]=[CH:14][CH:13]=1)=[N+:20]=[N-:21]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 33557Sodium AzideHCID 58999582HCID 58999582, compound

Product 1

HCID 589995844-Azido-5,6,7,8-tetrahydro-7-(phenylmethyl)-1,7-naphthyridineYield 55.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

7-Benzyl-4-chloro-5,6,7,8-tetrahydro-[1,7]naphthyridine (0.417 mmol) was treated with 5 equiv. of NaN3 (135 mg) in DMF (0.5 ml) and heated to 70° C. for 4 h. The residue was dissolved on 50 ml of DCM and washed with brine. The organic layer was concentrated to afford a black oil, which was purified by column chromatography to afford the desired azide (61 mg), which was used directly in the next step.

Workup

  1. washwashed with brine
  2. concentrationThe organic layer was concentrated
  3. customto afford a black oil, which
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-befe6f3210474ede813f561aae26f9b3
Source dataset
uspto-grants-2007_11
Patent number
US07297700B2

Reaction notes

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