Triethylamine → (1-Benzo[1,3]dioxol-5-yl-1,3,4,9-tetrahydro-beta-carbolin-2-yl)-[5-(3-trifluoromethyl-phenyl)-furan-2-yl]-methanone

HRID 983416

Reaction equation

HRID 983416 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:46]4[NH:45][C:44]5[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=5)[C:38]=4[CH2:37][CH2:36][NH:35]3)=[CH:28][C:27]=2[O:26]1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH2:25]1[O:33][C:32]2[CH:31]=[CH:30][C:29]([CH:34]3[C:46]4[NH:45][C:44]5[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=5)[C:38]=4[CH2:37][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

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2011721-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-beta-carbolineHCID 6882815-(3-(Trifluoromethyl)phenyl)-2-furoic acid

Product 1

HCID 12020635(1-Benzo[1,3]dioxol-5-yl-1,3,4,9-tetrahydro-beta-carbolin-2-yl)-[5-(3-trifluoromethyl-phenyl)-furan-2-yl]-methanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 5-(3-trifluoromethylphenyl)furoic acid (256 mg, 1 mmol) in DCM (20 mL, anhydrous) was added oxalyl chloride (165 mg, 1.3 mmol), followed by two drops of DMF. The mixture was stirred at room temperature for 1 h. A solution of 1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline (292 mg, 1 mmol) (prepared according to the process as disclosed in WO97/43287, Intermediate 7, page 24) and triethylamine (0.4 mL) in DCM (10 mL, anhydrous) was added and the mixture was stirred at room temperature for 16 h, washed sequentially with aqueous NaHCO3, brine (2×), 1N HCl and brine (2×) and dried with MgSO4. After evaporation of the solvent, a white solid was obtained.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 16 h
  3. washwashed sequentially with aqueous NaHCO3, brine (2×), 1N HCl and brine (2×)
  4. dry with materialdried with MgSO4
  5. customAfter evaporation of the solvent
  6. customa white solid was obtained

Sources & evidence

ORD record
ord-3d91dc99fc354d4f99eb42b7ef3fbacb
Source dataset
uspto-grants-2005_03
Patent number
US06864253B2

Linked notes

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