Sodium Carbonate → HCID 76281869, compound

HRID 929817Notes

Reaction equation

HRID 929817 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH:25]([C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:37]=[C:36]([C:38]([NH2:40])=[O:39])[O:35][N:34]=2)=[CH:29][CH:28]=1)=O.C([O-])([O-])=O.[Na+].[Na+]>ClC(Cl)C.CC(O)=O>[N:1]1([CH2:25][C:27]2[CH:28]=[CH:29][C:30]([C:33]3[CH:37]=[C:36]([C:38]([NH2:40])=[O:39])[O:35][N:34]=3)=[CH:31][CH:32]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 694601,2,3,4-TetrahydroquinolineHCID 5049666Sodium triacetoxyborohydrideHCID 90202333HCID 90202333, compound2×

Product 1

HCID 76281869HCID 76281869, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolvent2×

Procedure

To a solution of tetrahydroquinoline (20 μL, 0.16 mmol) in dichloroethane (1 mL) was added Na(OAc)3BH (88 mg, 0.415 mmol). The mixture was stirred at room temperature under argon for 20 min. A slurry of 3-(4-formyl-phenyl)-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 20; 20 mg, 0.093 mmol) in dichloroethane (1 mL) was added, followed by AcOH (20 μL). The reaction mixture was stirred at room temperature overnight. 1 M Na2CO3 solution was added and the mixture was extracted with CHCl3 (3×25 mL). The combined organic layers were washed with brine, dried (Na2SO4), evaporated, and purified by chromatography (11-20% acetone/CH2Cl2) to give 3-[4-(3,4-dihydro-2H-quinolin-1-ylmethyl)-phenyl]-isoxazole-5-carboxylic acid amide (21 mg, 45%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.35 (br. s., 1H), 7.97 (br. s., 1H), 7.84 (d, J=8.2 Hz, 2H), 7.47-7.57 (m, 1H), 7.38 (d, J=7.8 Hz, 2H), 6.72-6.93 (m, 2H), 6.36-6.50 (m, 2H), 4.53 (s, 2H), 3.34-3.43 (m, 2H), 2.73 (t, J=6.2 Hz, 2H), 1.93 (dt, J=11.2, 5.7 Hz, 2H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with CHCl3 (3×25 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. custompurified by chromatography (11-20% acetone/CH2Cl2)

Sources & evidence

ORD record
ord-6856e85bb30845b38b25cf983c390551
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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