3-[1-Cyclopropyl-1-(4-fluorophenyl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole → 3-[1-(4-Chloro-2-fluorophenyl)-1-cyclopropylethyl]-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561580Notes

Reaction equation

HRID 561580 reaction equation
ClC1C=C(Cl)C=CC=1C([C:13]1[C:21]2[C:16](=[C:17]([CH2:23][S:24][CH3:25])[CH:18]=[C:19](F)[CH:20]=2)[NH:15][CH:14]=1)CCO.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([CH:36]2[CH2:38][CH2:37]2)(O)[CH3:34])=[C:29]([F:39])[CH:28]=1.C1(C(C2C3C(=C(CSC)C=CC=3)NC=2)(C2C=CC(F)=CC=2)C)CC1>>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([C:13]2[C:21]3[C:16](=[C:17]([CH2:23][S:24][CH3:25])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)([CH:36]2[CH2:38][CH2:37]2)[CH3:34])=[C:29]([F:39])[CH:28]=1

Participants

4

Reactant 3

HCID 583921063-[1-Cyclopropyl-1-(4-fluorophenyl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indoleHCID 583923053-(2,4-Dichlorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-olHCID 583923431-(4-Chloro-2-fluorophenyl)-1-cyclopropylethanol

Product 1

HCID 583922333-[1-(4-Chloro-2-fluorophenyl)-1-cyclopropylethyl]-7-[(methylsulfanyl)methyl]-1H-indole

Conditions

Temperature
0 °C

Procedure

The title compound was prepared starting from 3.00 g (16.92 mmol) of the compound from Example 8 and 4.00 g (18.62 mmol) of the compound from Example 79A in analogy to the synthesis of the compound from Example 95. As a difference, the reaction mixture was stirred at 0° C. for 2 h and then warmed to RT. 1.54 g (24% of theory) of the target compound were obtained.

Workup

  1. temperaturewarmed to RT
  2. custom1.54 g (24% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-1fb0e8ba49c944b59564bd4b47221294
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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