4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane → 7-(Prop-1-en-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 578759Notes

Reaction equation

HRID 578759 reaction equation
Br[C:2]1[N:10]2[C:5]([C:6]([NH2:11])=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:12][C:13]1(C)[C:17](C)(C)OB(C(C)=C)O1>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:12]=[C:13]([C:2]1[N:10]2[C:5]([C:6]([NH2:11])=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1)[CH3:17]

Participants

8

Reactant 2

HCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 422813837-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine

Product 1

HCID 682061467-(Prop-1-en-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Reagents, catalysts & solvents 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

Under an argon atmosphere, 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (426 mg, 2 mmol) and 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (420 mg, 2.5 mmol) were dissolved in a mixture of 1,2-dimethoxyethane (10 mL) and aqueous sodium carbonate solution (2 M, 4 mL). The reaction mixture was degassed, and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride (73 mg, 0.1 mmol) was added. After stirring at 90° C. overnight, the reaction mixture was diluted with ethyl acetate (40 mL), water (10 mL) was added, and the layers were separated. The aqueous layer was extracted with ethyl acetate (2×40 mL), and the combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (puriFlash, Interchim, cyclohexane/ethyl acetate 1:1 to 100% ethyl acetate gradient) to yield the title product as a slightly yellow solid. Yield: 304 mg (81% of th.).

Workup

  1. customThe reaction mixture was degassed
  2. additionwas added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×40 mL)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (puriFlash, Interchim, cyclohexane/ethyl acetate 1:1 to 100% ethyl acetate gradient)

Sources & evidence

ORD record
ord-4f6869cc7e4345789af11c8f90f6b8ba
Source dataset
uspto-grants-2015_05
Patent number
US09040691B2

Reaction notes

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