Ytterbium triflate → Methyl 6-chloro-4-(3-chlorophenyl)-2-cyclopropylquinoline-3-carboxylate

HRID 1497042Notes

Reaction equation

HRID 1497042 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)=O.[CH:18]1([C:21](=O)[CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:20][CH2:19]1.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(O)C>[CH3:26][O:25][C:23]([C:22]1[C:21]([CH:18]2[CH2:20][CH2:19]2)=[N:1][C:2]2[C:3]([C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)=[CH:4][C:5]([Cl:8])=[CH:6][CH:7]=2)=[O:24]

Participants

5

Reactant 3

HCID 2733225Ytterbium triflateHCID 5231029(2-Amino-5-chlorophenyl)(3-chlorophenyl)methanoneHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl Ester

Product 1

HCID 86682924Methyl 6-chloro-4-(3-chlorophenyl)-2-cyclopropylquinoline-3-carboxylateYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of (2-amino-5-chlorophenyl)(3-chlorophenyl) methanone (81 mg, 0.31 mmol, 1 eq) and methyl 3-cyclopropyl-3-oxopropanoate (56.2 mg, 0.40 mmol, 1.3 eq) in ethanol (3 ml) was added ytterbium triflate (19 mg, 0.03 mmol, 0.1 eq) and the yellow solution was stirred overnight at room temperature. The resultant precipitate was filtered and washed with a small amount of ethanol to give the desired product (49 mg, 43%) as a white solid which did not require any further purification. MS (ESI): 372.1 (M+H)+.

Workup

  1. filtrationThe resultant precipitate was filtered
  2. washwashed with a small amount of ethanol

Sources & evidence

ORD record
ord-83dd73c5ebe94ae48768693d2a42eee5
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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