Tetrahydrofuran → HCID 178468649, compound

HRID 1893468Notes

Reaction equation

HRID 1893468 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]1[CH:13]=[CH:14][N:15]=[C:8]1[C:7]([N:16](C#C[Si](C)(C)C)[CH2:17][CH2:18][CH2:19][OH:20])=[N:6]2.[N+:29](=[CH:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[N-:30].[F-].[Cs+].[CH2:39]1COC[CH2:40]1>>[CH2:35]([O:34][C:32]([C:31]1[CH:40]=[C:39]([C:13]2[N:9]3[C:10]4[C:5]([N:6]=[C:7]([NH:16][CH2:17][CH2:18][CH2:19][OH:20])[C:8]3=[N:15][CH:14]=2)=[CH:4][C:3]([C:2]([F:1])([F:27])[F:28])=[CH:12][CH:11]=4)[NH:30][N:29]=1)=[O:33])[CH3:36]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 12192Ethyl diazoacetateHCID 25953Cesium fluorideHCID 68665711HCID 68665711, compound

Product 1

HCID 178468649HCID 178468649, compoundYield 35%

Procedure

A mixture of 3-(7-Trifluoromethyl-1-trimethylsilanylethynyl-imidazo[1,2-a]quinoxalin-4-ylamino)-propan-1-ol (0.37 mmol; 150 mg), ethyl diazoacetate (0.93 mmol; 0.10 mL), and CsF (0.55 mmol; 84 mg), in THF (0.2 mL) under argon was stirred at 85° C. for 20 hr. After concentration in vacuo, the residue was purified by preparative TLC (dichloromethane/methanol) to yield the title compound as a white powder (58 mg; 0.13 mmol; 35%).

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was purified by preparative TLC (dichloromethane/methanol)

Sources & evidence

ORD record
ord-694915df356b4d23a94fe496520df834
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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