Triphenylphosphine → HCID 10265272, compound

HRID 1611676Notes

Reaction equation

HRID 1611676 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[NH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[C:24]([OH:31])[CH:25]=[CH:26][CH:27]=2)[N:22]=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1.[CH3:54][CH:55]([CH3:62])[CH2:56][CH2:57][CH:58](O)[CH2:59][CH3:60]>>[CH2:59]([CH:58]([O:31][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:23]=1[N:22]=[C:21]([NH2:20])[CH:30]=[CH:29]2)[CH2:57][CH2:56][CH:55]([CH3:62])[CH3:54])[CH3:60]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 867836-Methylheptan-3-olHCID 46537882-Amino-8-quinolinolHCID 5387121Dibenzyl azodicarboxylate

Product 1

HCID 10265272HCID 10265272, compound

Procedure

A 7.5 mL conical microwave vessel (Personal Chemistry) equipped with a septum cap and a magnetic stirring bar was charged with PS-PPh3 resin (Aldrich Chemical Co., Inc, 140 mg, 4.40 equiv), 2-amino-8-hydroxyquinoline (15.0 mg, 0.0960 mmol) and DBAD (69 mg, 3.2 equiv) and purged by passing a stream of N2 for 45 seconds. Anhydr. THF (1.5 mL) was added and contents of the vessel were stirred for 10 min. Then, neat 6-methyl-3-heptanol (4 equiv) was added to the vessel and the resulting suspension was irradiated in Personal Chemistry Smith Synthesizer (150° C. for 330 s; 300 W). The suspension was then filtered, and the resin washed with THF (3×3.0 mL). The filtrate and washings were combined and evaporated in vacuo. The residue was then treated with 6.0 mL of 4 M HCl in dioxane at room temperature for 4 h. The resulting solution was evaporated in vacuo. The residue was dissolved in 1.5 mL of a 1:1 mixture of DMSO/MeOH and purified by preparative reverse-phase HPLC. 1H NMR (500 MHz, CDCl3) δ ppm 7.96 (d, 1H), 7.29 (t, 1H), 7.19 (m, 1H), 7.10 (d, 1H), 7.05 (br d, 1H), 4.37 (m, 1H), 1.91 (m, 2H), 1.78 (m, 2H), 1.55 (m, 1H), 1.35 (m, 1H), 1.24 (m, 1H), 0.98 (t, 3H), 0.87 (m, 6H); MS (DCI/NH3) m/z 273 [M+H]+.

Workup

  1. customA 7.5 mL conical microwave vessel (Personal Chemistry) equipped with a septum
  2. customcap
  3. custompurged
  4. customfor 45 seconds
  5. additionTHF (1.5 mL) was added
  6. customthe resulting suspension was irradiated in Personal Chemistry Smith Synthesizer (150° C. for 330 s; 300 W)
  7. filtrationThe suspension was then filtered
  8. washthe resin washed with THF (3×3.0 mL)
  9. customevaporated in vacuo
  10. additionThe residue was then treated with 6.0 mL of 4 M HCl in dioxane at room temperature for 4 h
  11. customThe resulting solution was evaporated in vacuo
  12. dissolutionThe residue was dissolved in 1.5 mL of a 1:1 mixture of DMSO/MeOH
  13. custompurified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-422d8d0c53824405b40050f4795e8866
Source dataset
uspto-grants-2006_01
Patent number
US06989392B2

Reaction notes

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