Sodium Azide → HCID 59394483, compound

HRID 1971398Notes

Reaction equation

HRID 1971398 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([CH2:28]OS(C)(=O)=O)[CH:23]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1.[N-:36]=[N+:37]=[N-:38].[Na+]>CS(C)=O.C(Cl)Cl.O>[F:35][C:2]([F:34])([F:1])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([CH2:28][N:36]=[N+:37]=[N-:38])[CH:23]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 59394190HCID 59394190, compound

Product 1

HCID 59394483HCID 59394483, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methanesulfonic acid 4-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]pyridine-2-ylmethyl ester (505 mg, 1.03 mmol) and sodium azide (201 mg, 3.12 mmol) in DMSO (5 mL) is heated at 80° C. for 2 h. The mixture is then diluted with DCM (100 mL) and water. The organic layer is washed further with brine and then dried over anhydrous Na2SO4. Following concentration the residue is separated via FCC (20-90% EtOAc/heptane) to give the title compound. MS (ESI) m/z 453.1 (M+1).

Workup

  1. washThe organic layer is washed further with brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentration the residue
  4. customis separated via FCC (20-90% EtOAc/heptane)

Sources & evidence

ORD record
ord-33fc1389878f49b99f2ec1c254af5a94
Source dataset
uspto-grants-2013_04
Patent number
US08431584B2

Reaction notes

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