proline dl-form → 5-[(4-Chlorophenyl){5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 561383Notes

Reaction equation

HRID 561383 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]1([CH3:19])[O:18][C:16](=[O:17])[CH2:15][C:13](=[O:14])[O:12]1.N1CCCC1C(O)=O.[F:28][C:29]1[CH:30]=[C:31]2[C:35](=[C:36]([CH2:38][S:39][CH3:40])[CH:37]=1)[NH:34][CH:33]=[CH:32]2>C(#N)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([C:32]2[C:31]3[C:35](=[C:36]([CH2:38][S:39][CH3:40])[CH:37]=[C:29]([F:28])[CH:30]=3)[NH:34][CH:33]=2)[CH:15]2[C:16](=[O:17])[O:18][C:11]([CH3:19])([CH3:10])[O:12][C:13]2=[O:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 614proline dl-formHCID 77264-ChlorobenzaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 583922275-Fluoro-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583924625-[(4-Chlorophenyl){5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.62 g (4.41 mmol) of 4-chlorobenzaldehyde, 0.64 g (4.41 mmol) of Meldrum's acid and 24 mg (0.21 mmol) of D,L-proline were added to a solution of 1.00 g (4.20 mmol) of the compound from Example 11A in 34 ml of acetonitrile. The reaction mixture was stirred at RT overnight. It was concentrated to result in 2.21 g (73% of theory) of the title compound with a purity of 64% which were reacted without further purification.

Workup

  1. concentrationIt was concentrated

Sources & evidence

ORD record
ord-a0eaabdfe6644160b3a6433776630cae
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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