Water → HCID 86731235, compound

HRID 2277179Notes

Reaction equation

HRID 2277179 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]4[CH2:21][CH2:20]4)=[CH:13][CH:12]=3)[O:10][C:4]=2[CH:3]=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.O>CN(C=O)C.[Cu]I>[CH:19]1([CH2:18][O:17][C:14]2[CH:15]=[CH:16][C:11]([C:9]3[O:10][C:4]4[CH:3]=[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])[N:7]=[CH:6][C:5]=4[N:8]=3)=[CH:12][CH:13]=2)[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10986677tert-Butyl (2S)-but-3-yn-2-ylcarbamateHCID 86731236HCID 86731236, compound

Product 1

HCID 86731235HCID 86731235, compoundYield 13.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-chloro-2-(4-(cyclopropylmethoxy)phenyl) [1,3]oxazolo[4,5-c]pyridine (700 mg), tert-butyl (2S)-but-3-yn-2-ylcarbamate (1.13 g) and triethylamine (0.649 g) in DMF (10 mL) were added bistriphenylphosphinedichloropalladium(II) (163 mg) and copper(I) iodide (88.7 mg), and the mixture was stirred at 100° C. for 2 hr under an argon atmosphere. The reaction mixture was allowed to cool to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and subjected to silica gel column chromatography (NH, ethyl acetate). The solvent was evaporated under reduced pressure, and the obtained solid was washed with ethyl acetate to give the title compound (132 mg).

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. customThe solvent was evaporated under reduced pressure
  5. washthe obtained solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-beb092f8a1e8402e8755fb1ae1d3b1f2
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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