Triethylamine → HCID 68027531, compound

HRID 527934Notes

Reaction equation

HRID 527934 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:23])[C:16]3[CH:21]=[CH:20][C:19](Br)=[CH:18][N:17]=3)[CH2:11]2)=[N:3][CH:2]=1.[C:24]([Si:26]([CH3:29])([CH3:28])[CH3:27])#[CH:25].CCN(CC)CC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:14][CH2:13][C@@H:12]([N:15]([CH3:23])[C:16]3[CH:21]=[CH:20][C:19]([C:25]#[C:24][Si:26]([CH3:29])([CH3:28])[CH3:27])=[CH:18][N:17]=3)[CH2:11]2)=[N:3][CH:2]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 66765983HCID 66765983, compound

Product 1

HCID 68027531HCID 68027531, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Under N2, a mixture of (R)—N-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-5-bromo-N-methylpyridin-2-amine (0.22 g, 0.58 mmol), ethynyltrimethylsilane (0.22 mL, 1.6 mmol), Et3N (0.24 mL, 1.5 mmol), CuI (5.0 mg, 0.03 mmol), PdCl2(PPh3)2 (8.0 mg, 0.01 mmol) and PPh3 (3.0 mg, 0.01 mmol) in DMF (3.0 mL) was stirred at 90° C. for 4 h. The reaction was then cooled to ambient temperature, diluted with water (3 mL), extracted with ethyl acetate (2×10 mL). The combined extracts was washed with brine (2×6 mL), dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel to give the titled compound. MS (m/z): 295 (M+H)+.

Workup

  1. temperatureThe reaction was then cooled to ambient temperature
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. washThe combined extracts was washed with brine (2×6 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d6e48787ee8e4a5c807b4e80b4e47443
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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