Toluene → Ethyl 1-((1-methyl-1,2,3,4-tetrahydroquinolin-7-yl)methyl)-1H-pyrazole-4-carboxylate

HRID 928427Notes

Reaction equation

[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12]O)[CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[NH:14]1[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:16]=[N:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][N:14]3[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:16]=[N:15]3)[CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred, cooled (0° C.) solution of (1-methyl-1,2,3,4-tetrahydroquinolin-7-yl)methanol (200 mg, 0.733 mmol), ethyl 1H-pyrazole-4-carboxylate (103 mg, 0.733 mmol) and triphenylphosphine (289 mg, 1.100 mmol) in THF (10 ml) was added dropwise a 40% solution of DEAD in toluene (0.435 ml, 1.1 mmol). The reaction mixture was stirred for 2 h at 0° C., then over night at 20° C. Saturated aqueous NaHCO3 was added and the mixture was extracted with AcOEt. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound. The crude product was purified by preparative HPLC (Waters SunFire Prep C18 OBD 5 μm 30*100, Flow 40 mL/min, ACN: 2 min at 5%, then to 100% within 17.5 min, RT 10.00 min) to give the title compound. HPLC (Method H) Rt=2.919 min; MS (Method A) [M+H]+=300.0

Workup

waitover night at 20° C
extractionthe mixture was extracted with AcOEt
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a9f2698a60b649c69f57f9337a2affd9
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290485B2

Reaction notes

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