Triphenylphosphine → HCID 86620670, compound

HRID 2101956Notes

Reaction equation

HRID 2101956 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[C:8]([C:15]([F:18])([F:17])[F:16])[C:9]([C:13]#[N:14])=[CH:10][CH:11]=2)[CH:6]=[C:5]1[CH3:19].C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[F:61][C:62]([F:71])([F:70])[C:63]1[CH:64]=[CH:65][C:66](=O)[NH:67][CH:68]=1>C(Cl)Cl>[CH3:19][C:5]1[N:4]([CH2:3][CH2:2][O:1][C:66]2[CH:65]=[CH:64][C:63]([C:62]([F:71])([F:70])[F:61])=[CH:68][N:67]=2)[C:12]2[C:7]([CH:6]=1)=[C:8]([C:15]([F:18])([F:16])[F:17])[C:9]([C:13]#[N:14])=[CH:10][CH:11]=2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1474432-Hydroxy-5-(trifluoromethyl)pyridineHCID 5387121Dibenzyl azodicarboxylateHCID 67405191HCID 67405191, compound

Product 1

HCID 86620670HCID 86620670, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(2-hydroxyethyl)-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.130 g, 0.49 mmol) in CH2Cl2 (3 mL) at 0° C. was treated with DBAD (0.302 g, 1.31 mmol), PPh3 (0.343 g, 1.31 mmol) and 5-(trifluoromethyl)-2(1H)-pyridinone (0.87 g, 0.53 mmol). The mixture was allowed to slowly warm to rt and then stirred for 14 h. Concentration was followed by column chromatography (SiO2, hexanes/EtOAc) to afford the title compound (0.160 g): 1H NMR (400 MHz, CDCl3) δ 8.36 (s, 1H), 7.75 (dd, J=8.8 and 2.5 Hz, 1H), 7.56 (d, J=8.4 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 6.71 (d, J=8.8 Hz, 1H), 6.57 (s, 1H), 4.67 (t, J=5.6 Hz, 2H), 4.54 (t, J=5.6 Hz, 2H), 2.54 (s, 3H); MS (ES) m/z 414 (M+1).

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-09188ca3267d4abcb1e2e37f4fdc64da
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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