Tetrahydrofuran → HCID 66711729, compound

HRID 1262019Notes

Reaction equation

HRID 1262019 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.[CH3:14][S:15][C:16]1[N:21]=[CH:20][C:19]2=[CH:22][CH:23]=[C:24]([CH:25]=[O:26])[N:18]2[N:17]=1>C(OCC)(=O)C>[CH3:14][S:15][C:16]1[N:21]=[CH:20][C:19]2=[CH:22][CH:23]=[C:24]([CH:25]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[OH:26])[N:18]2[N:17]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 574160572-(Methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine-7-carbaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 66711729HCID 66711729, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.00 M of Phenylmagnesium bromide in Tetrahydrofuran (1.552 mL, 1.552 mmol) was added to a solution of 2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine-7-carbaldehyde (250.0 mg, 1.294 mmol) in Tetrahydrofuran (8.0 mL, 99 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature with stirring for 3 hours. The mixture was then diluted with ethyl acetate and quenched with saturated ammonium chloride. The resulting mixture was washed with water and the organic layer was extracted, dried over sodium sulfate and reduced. The resulting oil was then purified via Isco flash column chromatography (hexanes/ethyl acetate) to afford 340 mg of (2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl-methanol. 1H NMR (400 MHz, DMSO, d6) δ 8.90 (s, 1H), 7.43 (m, 2H), 7.32 (m, 2H), 6.93 (m, 1H), 6.88 (m, 1H), 6.24 (m, 1H), 6.14 (m, 1H), 3.29 (s, 4H).

Workup

  1. customquenched with saturated ammonium chloride
  2. washThe resulting mixture was washed with water
  3. extractionthe organic layer was extracted
  4. dry with materialdried over sodium sulfate
  5. customThe resulting oil was then purified via Isco flash column chromatography (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e4bbb4e5b01e45128cd0589f3274dece
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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