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

HRID 561385Notes

Reaction equation

HRID 561385 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[C:37]([CH2:38][S:39][CH3:40])=[C:36]2[C:32]([CH:33]=[CH:34][NH:35]2)=[CH:31][CH:30]=1>C(#N)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([C:33]2[C:32]3[C:36](=[C:37]([CH2:38][S:39][CH3:40])[C:29]([F:28])=[CH:30][CH:31]=3)[NH:35][CH:34]=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 583922596-Fluoro-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583925085-[(4-Chlorophenyl){6-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

1.44 g (10.24 mmol) of 4-chlorobenzaldehyde, 1.48 g (10.24 mmol) of Meldrum's acid and 0.06 g (0.51 mmol) of D,L-proline were added to a solution of 2.00 g (10.24 mmol) of the compound from Example 9A in 15 ml of acetonitrile. The reaction mixture was stirred at RT overnight. The precipitated solid was filtered off with suction, washed with acetonitrile and dried under high vacuum. 3.32 g (67% of theory) of the title compound were obtained.

Workup

  1. filtrationThe precipitated solid was filtered off with suction
  2. washwashed with acetonitrile
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-898bab17c81d4356aa22ad99be3677e3
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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