Oxalyl chloride → 3-Benzo[1,3]dioxol-5-yl-2-[5-(3-trifluoromethyl-phenyl)-furan-2-carbonyl]-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one

HRID 2415372Notes

Reaction equation

HRID 2415372 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([C:9]2[O:13][C:12]([C:14]([OH:16])=O)=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C(Cl)(=O)C(Cl)=O.[CH2:25]1[O:33][C:32]2[CH:31]=[CH:30][C:29]([CH:34]3[C:38]4[NH:39][C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][C:45]=5[C:46](=[O:47])[C:37]=4[CH2:36][NH:35]3)=[CH:28][C:27]=2[O:26]1>CN(C=O)C.CN(C1C=CN=CC=1)C.C(OCC)(=O)C.C1COCC1.C(Cl)Cl.C(N(CC)CC)C>[CH2:25]1[O:33][C:32]2[CH:31]=[CH:30][C:29]([CH:34]3[C:38]4[NH:39][C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][C:45]=5[C:46](=[O:47])[C:37]=4[CH2:36][N:35]3[C:14]([C:12]3[O:13][C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:18])[F:17])[CH:4]=4)=[CH:10][CH:11]=3)=[O:16])=[CH:28][C:27]=2[O:26]1

Participants

10

Reactant 3

HCID 65578Oxalyl chlorideHCID 6882815-(3-(Trifluoromethyl)phenyl)-2-furoic acidHCID 108921213-(1,3-benzodioxol-5-yl)-1,2,3,4-tetrahydro-9H-pyrrolo[3,4-b]quinolin-9-one

Product 1

HCID 129930273-Benzo[1,3]dioxol-5-yl-2-[5-(3-trifluoromethyl-phenyl)-furan-2-carbonyl]-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one

Reagents, catalysts & solvents 6

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(3-trifluoromethylphenyl)-2-furoic acid (80.44 mg, 0.314 mmol) in 1:1 DCM:THF (5 mL, anhydrous) was added oxalyl chloride (43.85 mg, 0.345 mmol), followed by two drops of DMF. The mixture was stirred at room temperature for 1 h. A suspension of 1,2,3,4-tetrahydro-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one (96.2 mg, 0.314 mmol) (prepared as in Example 5), triethylamine (0.13 mL), and DMAP (trace) in 1:1 DCM:THF (5 mL) was added. The resulting mixture was stirred at room temperature for 16 h. Ethyl acetate (50 mL) was added, and the solution was washed with aq. NaHCO3, brine, 1N HCl, brine and then dried with MgSO4. The solvent was evaporated and the residue triturated with ethyl acetate to yield the product as a white solid.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 16 h
  2. washthe solution was washed with aq. NaHCO3, brine, 1N HCl, brine
  3. dry with materialdried with MgSO4
  4. customThe solvent was evaporated
  5. customthe residue triturated with ethyl acetate

Sources & evidence

ORD record
ord-4fb185df734e4a649112f938214097f9
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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