Triphenylphosphine → 2-{4-[4-Pyridin-4-yl-1-(2,2,2-trifluoro-ethyl)-1H-pyrazol-3-yl]-phenoxymethyl}-quinoxaline

HRID 33893Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[N:9][N:10]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH:11]=2)=[CH:3][CH:2]=1.[N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=[CH:26][C:25]=1[CH2:34]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>O1CCOCC1>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH2:34][C:25]4[CH:26]=[N:27][C:28]5[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=5)[N:24]=4)=[CH:21][CH:22]=3)=[N:9][N:10]([CH2:12][C:13]([F:15])([F:16])[F:14])[CH:11]=2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-[4-Pyridin4-yl-1-(2,2,2-trifluoro-ethyl)-1H-pyrazol-3-yl]-phenol (79 mg) and Quinoxalin-2-yl-methanol (50 mg) in dioxane (2 ml) was added triphenylphosphine (105 mg) and di-t-butyldiazacarboxalate (92 mg) and the reaction mixture heated at 60° C. After 18, the reaction mixture was poured into 1N NaOH, extracted with methylene chloride, dried magnesium sulfate, filtered and concentrated. Purification with MPLC biotage eluting with 2% methanol/0.5% ammonium hydroxide/60% ethyl acetate/hexanes provided the title compound (54 mg). 1H NMR (400 MHz, CDCl3) δ 9.09 (s, 1 H), 8.52 (m, 2H), 8.13 (m, 1H), 8.10 (m, 1H), 7.79 (m, 2 H), 7.73 (s, 1 H), 7.40 (d, J=8.7, Hz, 2 H), 7.24 (m, 2H), 7.04 (d, J=8.7 Hz, 2 H), 5.32 (s, 2H), 4.79 (q, J=8.3 Hz, 2 H); MS: (M+H m/z=462.1).

Workup

extractionextracted with methylene chloride, dried magnesium sulfate
filtrationfiltered
concentrationconcentrated
customPurification with MPLC biotage
washeluting with 2% methanol/0.5% ammonium hydroxide/60% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-1a5a0f08af6e45169c10c048fcda5f32
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429665B2

Reaction notes

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