Triphenylphosphine → HCID 54575340, compound

HRID 1519241Notes

Reaction equation

HRID 1519241 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH2:21][OH:22])=[N:6][CH:7]=1.[NH:23]1[C:31]2[C:26](=[CH:27][C:28](O)=[CH:29][CH:30]=2)[CH:25]=[N:24]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>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH2:21][O:22][C:28]2[CH:27]=[C:26]3[C:31](=[CH:30][CH:29]=2)[NH:23][N:24]=[CH:25]3)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1014381H-Indazol-5-olHCID 5363146Diisopropyl azodicarboxylateHCID 71184222HCID 71184222, compound2×

Product 1

HCID 54575340HCID 54575340, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methanol (intermediate B1.1, 0.12 g, 0.36 mmol) in THF (3 ml) was added 1H-indazole-5-ol (0.1 g, 0.71 mmol), Ph3P (0.19 g, 0.71 mmol) and DIAD (0.14 ml, 0.71 mmol). The reaction was stirred at rt for 3 h, concentrated and purified by flash chromatography (silica, 30-60% EtOAc/hexanes) to give 5-({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methoxy)-1H-indazole as white solid. 1H NMR (400 MHz, CDCl3) δ 9.95 (s, 1H), 8.32 (d, J=2.5 Hz, 1H), 8.10 (m, 2H), 7.89 (s, 1H), 7.32 (m, 2H), 7.23 (d, J=2.2 Hz, 1H), 7.15 (t, J=8.6 Hz, 2H), 7.09 (m, 1H), 5.17 (s, 2H); HRMS exact mass talc for C22H14ClFN4O2S [M+H]+: 453.0583; observed: 453.0584.

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography (silica, 30-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4d283ddd4dbf47ab9a705702d84a6eac
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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