Triphenylphosphine → HCID 71062664, compound

HRID 1524189Notes

Reaction equation

HRID 1524189 reaction equation
[N:1]1([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][C@H:14]([CH2:18][OH:19])[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH3:53][C:54]1[C:59](O)=[CH:58][CH:57]=[CH:56][N:55]=1>C1COCC1>[N:1]1([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][C@H:14]([CH2:18][O:19][C:59]3[C:54]([CH3:53])=[N:55][CH:56]=[CH:57][CH:58]=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 707192-Methylpyridin-3-olHCID 5363146Diisopropyl azodicarboxylateHCID 71062870HCID 71062870, compound

Product 1

HCID 71062664HCID 71062664, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesised in essentially the same way as compound 18s. Compound 51 (Example 10; 80 mg, 0.30 mmol) and PPh3 (120 mg, 0.46 mmol) were dissolved in dry THF (1.5 ml). Then DIAD (90 μl, 0.46 mmol) and 2-methyl-3-hydroxypyridine (50 mg, 0.46 mmol) were added. The reaction mixture was stirred at RT for 48 hrs. After this time, the solvent was removed and the crude mixture purified by flash column chromatography (silica, DCM/MeOH 1:0 to 94:6) to afford compound 26s (75 mg, 71%). Analyses were performed on the free base. The compound was converted to the HCl salt for testing.

Workup

  1. customAfter this time, the solvent was removed
  2. customthe crude mixture purified by flash column chromatography (silica, DCM/MeOH 1:0 to 94:6)

Sources & evidence

ORD record
ord-5f3e625530e04eef8ded4f254dd5ed49
Source dataset
uspto-grants-2015_07
Patent number
US09079895B2

Reaction notes

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