Tetrahydrofuran → HCID 118251610, compound

HRID 2203181Notes

Reaction equation

HRID 2203181 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:13]=[C:14]([Cl:25])[CH:15]=[C:16]3[C:20]=1[N:19]([CH2:21][CH:22]([CH3:24])[CH3:23])[N:18]=[CH:17]3)[C:6](=[O:26])[CH2:5]2.CC1(C)C2[C:49](=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)[O:48][C:30]2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(N(CC)CC)C.[O:76]1CCCC1>CO.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[CH3:30][O:48][C:49]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:13]=[C:14]([Cl:25])[CH:15]=[C:16]3[C:20]=1[N:19]([CH2:21][CH:22]([CH3:23])[CH3:24])[N:18]=[CH:17]3)[C:6](=[O:26])[CH2:5]2)=[O:76]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 118251652HCID 118251652, compound

Product 1

HCID 118251610HCID 118251610, compound

Reagents, catalysts & solvents 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of compound 64 (0.1 g, 0.231 mmol), molybdenumhexacarbonyl (0.03 g, 0.115 mmol), Hermann's catalyst (0.022 g, 0.023 mmol), Xantphos (0.027 g, 0.0426 mmol), triethylamine (0.643 mL, 0.462 mmol) in a mixture of tetrahydrofuran (3 mL) and methanol (0.9 mL) was heated at 150° C. under microwave conditions for 10 minutes. Then, the reaction was quenched by adding water and diluted with ethyl acetate. The organic layer was separated, washed with Brine, dried (MgSO4), filtered and the solvent was evaporated. Then, the residue was purified by chromatography column on a 20 g SPE cartridge to give the title compound as a colorless solid. (0.043 g, 45%)

Workup

  1. customThen, the reaction was quenched
  2. additionby adding water
  3. additiondiluted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with Brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThen, the residue was purified by chromatography column on a 20 g SPE cartridge

Sources & evidence

ORD record
ord-a79c1e0a01414b9f9dd6ddaf50121748
Source dataset
uspto-grants-2016_06
Patent number
US09365569B2

Reaction notes

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