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Ethanol → 6-Fluoro-3-[4-(4-iodo-3-methoxy-phenyl)-1,2,3-triazol-1-yl]-1,3,4,5-tetrahydro-1-benzazepin-2-one

HRID 2035700
Notes
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Reaction equation

HRID 2035700 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([I:9])=[C:5]([O:10][CH3:11])[CH:4]=1)#[CH:2].[N:12]([CH:15]1[CH2:21][CH2:20][C:19]2[C:22]([F:26])=[CH:23][CH:24]=[CH:25][C:18]=2[NH:17][C:16]1=[O:27])=[N+:13]=[N-:14].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].CCO>ClCCl.O.CN(C=O)C>[F:26][C:22]1[C:19]2[CH2:20][CH2:21][CH:15]([N:12]3[CH:2]=[C:1]([C:3]4[CH:8]=[CH:7][C:6]([I:9])=[C:5]([O:10][CH3:11])[CH:4]=4)[N:14]=[N:13]3)[C:16](=[O:27])[NH:17][C:18]=2[CH:25]=[CH:24][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 702EthanolHCID 190256673-Azido-6-fluoro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-oneHCID 23667548Sodium AscorbateHCID 866614654-Ethynyl-1-iodo-2-methoxybenzene

Product 1

HCID 666838136-Fluoro-3-[4-(4-iodo-3-methoxy-phenyl)-1,2,3-triazol-1-yl]-1,3,4,5-tetrahydro-1-benzazepin-2-oneYield 95.1%

Reagents, catalysts & solvents

3
HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

4-Ethynyl-1-iodo-2-methoxy-benzene (22.23 g, 86 mmol), 3-azido-6-fluoro-1,3,4,5-tetrahydro-1-benzazepin-2-one (20.87 g, 95 mmol), and sodium ascorbate (15.69 g, 86 mmol) were added to EtOH (155 mL) and DMF (155 mL). CuSO4.5H2O (10.75 g, 43.1 mmol) was added to 20 mL water and added dropwise to the stirring reaction mixture. The reaction stirred for 17 hrs at room temp. Dichloromethane was added and the organic layer was washed with 2N NaOH, dried with sodium sulfate and concentrated. Purification on silica gel (dichloromethane:methanol, 1-15%). 6-Fluoro-3-[4-(4-iodo-3-methoxy-phenyl)-1,2,3-triazol-1-yl]-1,3,4,5-tetrahydro-1-benzazepin-2-one (39.1 g) was obtained as a colorless solid and carried on the next step.

Workup

  1. additionadded dropwise to the stirring reaction mixture
  2. washthe organic layer was washed with 2N NaOH
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customPurification on silica gel (dichloromethane:methanol, 1-15%)

Sources & evidence

ORD record
ord-9279d1a0e83948498c2cfe39a75431e7
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08575150B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes