1-[2-(4-Iodophenoxy)ethyl]-4-methylpiperidin-4-ol → 1-(2-{4-[3-Fluoro-5-(4-methylcyclohex-1-enyl)pyridin-2-ylethynyl]phenoxy}ethyl)-4-methylpiperidin-4-ol

HRID 734894Notes

Reaction equation

HRID 734894 reaction equation
[C:1]([C:3]1[C:8]([F:9])=[CH:7][C:6]([C:10]2[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12][CH:11]=2)=[CH:5][N:4]=1)#[CH:2].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>>[F:9][C:8]1[C:3]([C:1]#[C:2][C:18]2[CH:34]=[CH:33][C:21]([O:22][CH2:23][CH2:24][N:25]3[CH2:26][CH2:27][C:28]([CH3:32])([OH:31])[CH2:29][CH2:30]3)=[CH:20][CH:19]=2)=[N:4][CH:5]=[C:6]([C:10]2[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12][CH:11]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 578453271-[2-(4-Iodophenoxy)ethyl]-4-methylpiperidin-4-olHCID 860769852-Ethynyl-3-fluoro-5-(4-methylcyclohex-1-enyl)pyridine

Product 1

HCID 578452931-(2-{4-[3-Fluoro-5-(4-methylcyclohex-1-enyl)pyridin-2-ylethynyl]phenoxy}ethyl)-4-methylpiperidin-4-ol

Procedure

The product was prepared analogously to Example 48.1c from 130 mg (0.60 mmol) of 2-ethynyl-3-fluoro-5-(4-methylcyclohex-1-enyl)pyridine and 217 mg (0.60 mmol) of 1-[2-(4-iodophenoxy)ethyl]-4-methylpiperidin-4-ol (IP 15) (24 at RT, triethylamine as base). Yield: 15 mg (6% of theoretical); C28H33FN2O2 (M=448.572); calc.: molpeak (M+H)+:449; found: molpeak (M+H)+:449; HPLC-MS: 5.08 minutes (method H).

Workup

  1. custom5.08 minutes (method H)

Sources & evidence

ORD record
ord-d57a81b984c943899a93d7461666757c
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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