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

HRID 928421Notes

Reaction equation

HRID 928421 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15]O)[CH:13]=2)[CH2:8][CH2:7][CH2:6]1.[NH:17]1[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:19]=[N:18]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>C1COCC1.CCOC(C)=O>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][N:17]3[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:19]=[N:18]3)[CH:13]=2)[CH2:8][CH2:7][CH2:6]1

Participants

8

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 58081319(1-(2-Methoxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl)methanol

Product 1

HCID 58081306Ethyl 1-((1-(2-methoxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl)methyl)-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(1-(2-Methoxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl)methanol (357 mg, 0.807 mmol) and ethyl 1H-pyrazole-4-carboxylate (113 mg, 0.807 mmol) were dissolved in THF (5 ml). Triphenylphosphine (317 mg, 1.210 mmol) was added, and, after cooling to 0° C., a 40% solution of DEAD in Toluene (0.479 ml, 1.210 mmol) was added dropwise. The reaction mixture was stirred for 2 hr at 0° C., then overnight at 20° C. The reaction mixture was diluted with AcOEt and washed with 1N HCl, and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by preparative-HPLC (Waters SunFire Prep C18 OBD 5 μm 19*50, Flow 20 mL/min, ACN: 2 min at 5%, then to 100% within 17.5 min, RT 11.80 min) to give the title compound. HPLC (Method A) Rt=2.001 min; MS (Method A) [M]+=343.9

Workup

  1. customovernight
  2. customat 20° C
  3. washwashed with 1N HCl, and saturated aqueous NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by preparative-HPLC (Waters SunFire Prep C18 OBD 5 μm 19*50, Flow 20 mL/min, ACN
  7. wait2 min at 5%, then to 100% within 17.5 min

Sources & evidence

ORD record
ord-6b8530318de9443292e83db9ee2afa1b
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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