Dimethylformamide → 6-fluoro-3-{4-[4-(pyridin-3-yloxy)phenyl]-1H-1,2,3-triazol-1-yl}-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

HRID 2035710Notes

Reaction equation

HRID 2035710 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=CC=2)[CH:2]=1.O=[C:17]1O[C@H]([C@H](CO)O)C([O-])=[C:18]1O.[Na+].[N:29]([CH:32]1[CH2:38][CH2:37][C:36]2[C:39]([F:43])=[CH:40][CH:41]=[CH:42][C:35]=2[N:34]([CH2:44][C:45]([F:48])([F:47])[F:46])[C:33]1=[O:49])=[N+:30]=[N-:31].CN(C=O)C>O.CCOC(C)=O.CCO>[F:43][C:39]1[C:36]2[CH2:37][CH2:38][CH:32]([N:29]3[CH:18]=[C:17]([C:15]4[CH:10]=[CH:9][C:8]([O:7][C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)=[CH:13][CH:14]=4)[N:31]=[N:30]3)[C:33](=[O:49])[N:34]([CH2:44][C:45]([F:48])([F:46])[F:47])[C:35]=2[CH:42]=[CH:41][CH:40]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 23667548Sodium AscorbateHCID 58063523HCID 58063523, compoundHCID 666830994-(Pyridine-3-yloxy)ethynylbenzene

Product 1

HCID 580635646-fluoro-3-{4-[4-(pyridin-3-yloxy)phenyl]-1H-1,2,3-triazol-1-yl}-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-(Pyridine-3-yloxy)ethynylbenzene (50 mg, 0.256 mmol), cupric sulfate (12.26 mg, 0.077 mmol), sodium ascorbate (20.30 mg, 0.102 mmol), and 3-azido-6-fluoro-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (93 mg, 0.307 mmol) in 2.5 mL of a 1:1:1 solution of DMF:EtOH:H2O was stirred for 25 mins. The mixture was diluted with water and EtOAc was added to extract the product. The organic phase was separated and washed with water (2×) and brine (1×) before being dried with Na2SO4 and evaporated to afford an oil. This material was chromatographed on silica (0-80% EtOAc in hexanes to yield 75.7 mg as a solid.

Workup

  1. additionwas added
  2. extractionto extract the product
  3. customThe organic phase was separated
  4. washwashed with water (2×) and brine (1×)
  5. dry with materialbefore being dried with Na2SO4
  6. customevaporated
  7. customto afford an oil
  8. customThis material was chromatographed on silica (0-80% EtOAc in hexanes
  9. customto yield 75.7 mg as a solid

Sources & evidence

ORD record
ord-f7d21d74e182445a8f927d3e2b329544
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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