5-(4-Chlorophenyl)-2-iodopyridine → (5-{4-[5-(4-Chlorophenyl)pyridin-2-yl]but-3-ynyl}pyridin-2-yl)isopropylamine

HRID 734904Notes

Reaction equation

HRID 734904 reaction equation
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][CH:12]([CH3:14])[CH3:13])=[N:9][CH:10]=1)[CH2:2][C:3]#[CH:4].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[CH:24][C:25](I)=[N:26][CH:27]=2)=[CH:18][CH:17]=1>>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:23]=[CH:24][C:25]([C:4]#[C:3][CH2:2][CH2:1][C:5]3[CH:6]=[CH:7][C:8]([NH:11][CH:12]([CH3:14])[CH3:13])=[N:9][CH:10]=3)=[N:26][CH:27]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 859698495-(4-Chlorophenyl)-2-iodopyridineHCID 86076998HCID 86076998, compound

Product 1

HCID 57845312(5-{4-[5-(4-Chlorophenyl)pyridin-2-yl]but-3-ynyl}pyridin-2-yl)isopropylamine

Procedure

The product was prepared analogously to Example 50.5d from 100 mg (0.53 mmol) of (5-but-3-ynylpyridin-2-yl)isopropylamine and 168 mg (0.53 mmol) of 5-(4-chlorophenyl)-2-iodopyridine (purification by preparative HPLC-MS). Yield: 520 mg (54% of theoretical); C23H22ClN3 (M=375.894); calc.: molpeak (M+H)+:376/378; found: molpeak (M+H)+:376/378; HPLC-MS: 5.33 minutes (method G).

Workup

  1. custom5.33 minutes (method G)

Sources & evidence

ORD record
ord-7c04f7a3d5aa44e5a1ccd4d1d0a95461
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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