(4-Chlorophenyl)(4-fluorophenyl)methanol → 3-[(4-Chlorophenyl)(4-fluorophenyl)methyl]-5-fluoro-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561708Notes

Reaction equation

HRID 561708 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][S:12][CH3:13])[CH:10]=1)[NH:7][CH:6]=[CH:5]2.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)O)=[CH:17][CH:16]=1.FC1C=CC(C(C2C=CC(F)=CC=2)C2C3C(=C(CSC)C=CC=3)NC=2)=CC=1>>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH:21]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:5]2[C:4]3[C:8](=[C:9]([CH2:11][S:12][CH3:13])[CH:10]=[C:2]([F:1])[CH:3]=3)[NH:7][CH:6]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 12634874(4-Chlorophenyl)(4-fluorophenyl)methanolHCID 583921273-[Bis(4-fluorophenyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indoleHCID 583922275-Fluoro-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583921723-[(4-Chlorophenyl)(4-fluorophenyl)methyl]-5-fluoro-7-[(methylsulfanyl)methyl]-1H-indole

Conditions

Temperature
80 °C

Procedure

The title compound was prepared starting from 500 mg (2.56 mmol) of the compound from Example 11A and 667 mg (2.56 mmol) of the compound from Example 81A in analogy to the synthesis of the compound from Example 278. A difference was that stirring at 80° C. was for only 4 h. 535 mg (50% of theory) of the target compound were obtained.

Workup

  1. custom535 mg (50% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-96b97a45989947df83e8d72184099e7e
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…