Potassium Carbonate → (S)-tert-Butyl (1-(5-((3-fluoro-4-methoxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate

HRID 1052434Notes

Reaction equation

HRID 1052434 reaction equation
I[C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C@@H:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19])=[N:6]2.[F:28][C:29]1[CH:30]=[C:31]([SH:37])[CH:32]=[CH:33][C:34]=1[O:35][CH3:36].C(=O)([O-])[O-].[K+].[K+]>[Cu]I>[F:28][C:29]1[CH:30]=[C:31]([S:37][C:2]2[CH:3]=[CH:4][N:5]3[C:10]=2[C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([C@@H:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19])=[N:6]3)[CH:32]=[CH:33][C:34]=1[O:35][CH3:36]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27590073-Fluoro-4-methoxythiophenolHCID 131736123HCID 131736123, compound

Product 1

HCID 131736157(S)-tert-Butyl (1-(5-((3-fluoro-4-methoxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamateYield 71%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

(S)-tert-Butyl (1-(5-iodo-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate (286 mg, 0.60 mmol) was treated with 3-fluoro-4-methoxybenzenethiol (141 mg, 0.89 mmol), potassium carbonate (123 mg, 0.89 mmol) and copper(I) iodide (170 mg, 0.89 mmol) according to the method described in Preparation 44. The crude was purified using SP1® Purification System (0%-25%, hexane-ethyl acetate) to give 226 mg (71% yield) to the title compound as an oil.

Workup

  1. customdescribed in Preparation 44
  2. customThe crude was purified
  3. customSP1® Purification System (0%-25%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1eeb1e07d67f4601b2ce523a9b03805c
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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