Dimethylformamide → HCID 86666293, compound

HRID 1026287Notes

Reaction equation

HRID 1026287 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:16]=[C:15]([O:17][CH2:18][CH:19]4[CH2:21][CH2:20]4)[CH:14]=[CH:13][C:11]=3[N:12]=2)=[N:6][CH:7]=1.[CH3:22][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:24]#[CH:25].C(N(CC)CC)C.CN(C=O)C>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.[Cu]I.O>[CH:19]1([CH2:18][O:17][C:15]2[CH:14]=[CH:13][C:11]3[N:12]=[C:8]([C:5]4[N:6]=[CH:7][C:2]([C:25]#[C:24][C@@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:22])=[CH:3][CH:4]=4)[O:9][C:10]=3[CH:16]=2)[CH2:21][CH2:20]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10986677tert-Butyl (2S)-but-3-yn-2-ylcarbamateHCID 67778724HCID 67778724, compound

Product 1

HCID 86666293HCID 86666293, compoundYield 59.7%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

Under an argon atmosphere, a mixture of 2-(5-bromopyridin-2-yl)-6-(cyclopropylmethoxy)-1,3-benzoxazole (200 mg), tert-butyl [(1S)-1-methylprop-2-yn-1-yl]carbamate (196 mg), dichlorobis(triphenylphosphine)palladium(II) (20.3 mg), copper(I) iodide (11.0 mg), triethylamine (0.081 mL) and DMF (5 mL) was stirred at 80° C. for 8 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a yellow powder (150 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ad8e7cf558cb4ffdbcbca94ee595eb87
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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