1-(2-(4-Iodophenoxy)ethyl)-4-methylpiperidine → 3-Fluoro-5-(4-methylcyclohex-1-enyl)-2-{4-[2-(4-methylpiperidin-1-yl)ethoxy]phenylethynyl}pyridine

HRID 734893Notes

Reaction equation

HRID 734893 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:33]=[CH:32][C:21]([O:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([CH3:31])[CH2:27][CH2:26]2)=[CH:20][CH:19]=1>C(N(CC)CC)C>[F:9][C:8]1[C:3]([C:1]#[C:2][C:18]2[CH:19]=[CH:20][C:21]([O:22][CH2:23][CH2:24][N:25]3[CH2:26][CH2:27][CH:28]([CH3:31])[CH2:29][CH2:30]3)=[CH:32][CH:33]=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

4

Reactant 2

HCID 690610171-(2-(4-Iodophenoxy)ethyl)-4-methylpiperidineHCID 860769852-Ethynyl-3-fluoro-5-(4-methylcyclohex-1-enyl)pyridine

Product 1

HCID 578452963-Fluoro-5-(4-methylcyclohex-1-enyl)-2-{4-[2-(4-methylpiperidin-1-yl)ethoxy]phenylethynyl}pyridine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

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 207 mg (0.60 mmol) of 1-[2-(4-iodophenoxy)ethyl]-4-methylpiperidine (Example 19.1 a) (24 at RT, triethylamine as base). Yield: 15 mg (6% of theoretical); C28H33FN2O (M=432.573); calc.: molpeak (M+H)+:433; found: molpeak (M+H)+:433; HPLC-MS: 5.60 minutes (method H).

Workup

  1. custom5.60 minutes (method H)

Sources & evidence

ORD record
ord-668267131e2c4a92804083240ffbc550
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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