1-[2-(4-Iodophenoxy)ethyl]-4-methylpiperidin-4-ol → 1-(2-{4-[5-(4-Chloro-2-methylphenyl)pyrazin-2-ylethynyl]phenoxy}ethyl)-4-methylpiperidin-4-ol

HRID 734889Notes

Reaction equation

HRID 734889 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][C:11]([C:14]#[CH:15])=[CH:10][N:9]=2)=[C:4]([CH3:16])[CH:3]=1.I[C:18]1[CH:34]=[CH:33][C:21]([O:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][C:28]([CH3:32])([OH:31])[CH2:27][CH2:26]2)=[CH:20][CH:19]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11]([C:14]#[C:15][C:18]3[CH:34]=[CH:33][C:21]([O:22][CH2:23][CH2:24][N:25]4[CH2:26][CH2:27][C:28]([CH3:32])([OH:31])[CH2:29][CH2:30]4)=[CH:20][CH:19]=3)=[N:12][CH:13]=2)=[C:4]([CH3:16])[CH:3]=1

Participants

3

Reactant 2

HCID 578453271-[2-(4-Iodophenoxy)ethyl]-4-methylpiperidin-4-olHCID 860769812-(4-Chloro-2-methylphenyl)-5-ethynylpyrazine

Product 1

HCID 578453001-(2-{4-[5-(4-Chloro-2-methylphenyl)pyrazin-2-ylethynyl]phenoxy}ethyl)-4-methylpiperidin-4-ol

Procedure

The product was prepared analogously to Example 48.1c from 200 mg (0.88 mmol) of 2-(4-chloro-2-methylphenyl)-5-ethynylpyrazine and 316 mg (0.88 mmol) of 1-[2-(4-iodophenoxy)ethyl]-4-methylpiperidin-4-ol (IP 15) (stirring the reaction mixture overnight at RT). Yield: 30 mg (7% of theoretical); C27H28ClN3O2 (M=461.983); calc.: molpeak (M+H)+:462/464 (Cl); found: molpeak (M+H)+:462/464 (Cl); HPLC-MS: 5.43 minutes (method G; Zorbax-Bonus).

Workup

  1. custom5.43 minutes (method G; Zorbax-Bonus)

Sources & evidence

ORD record
ord-ebd32bd4dea14e7182cc5dfe50be1dc9
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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