Sodium Carbonate → HCID 56646065, compound

HRID 2040849Notes

Reaction equation

HRID 2040849 reaction equation
Br[C:2]1[CH2:6][C:5]2([CH2:11][CH2:10][N:9]([C:12]3[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[C:14]([CH3:21])[N:13]=3)[CH2:8][CH2:7]2)[O:4][N:3]=1.[CH3:22][CH:23]([CH3:26])[C:24]#[CH:25].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH3:22][CH:23]([CH3:26])[C:24]#[C:25][C:2]1[CH2:6][C:5]2([CH2:11][CH2:10][N:9]([C:12]3[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[C:14]([CH3:21])[N:13]=3)[CH2:8][CH2:7]2)[O:4][N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium Carbonate2×HCID 690193-Methylbut-1-yne2×HCID 86762124HCID 86762124, compound

Product 1

HCID 56646065HCID 56646065, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of Compound 19a (50 mg, 0.141 mmol), 3-methyl-1-butyne (48 mg, 0.705 mmol), sodium carbonate (74.6 mg, 0.704 mmol) and Cu (44.8 mg, 0.705 mmol) was heated in a sealed vessel at 120° C. for 32 h, adding every 8 h additional equal amounts of amounts of 3-methyl-1-butyne, sodium carbonate and Cu. Afterwards, the mixture was cooled, added with CH2Cl2, filtered on celite and evaporated to dryness in vacuo. The residue was purified by automated flash chromatography (SP1®TM-Biotage; gradient Petroleum Ether-EtOAc from 95:5 to 75:25 then isocratic Petroleum Ether-EtOAc from 9:1 giving 16 mg of the title product. Yield: 33.1%.

Workup

  1. temperatureAfterwards, the mixture was cooled
  2. filtrationfiltered on celite
  3. customevaporated to dryness in vacuo
  4. customThe residue was purified by automated flash chromatography (SP1®TM-Biotage

Sources & evidence

ORD record
ord-ff2f3577a1d64a34bdaddf7611b565a4
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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