3-Iodopyridine → HCID 54757836, compound

HRID 2042988Notes

Reaction equation

HRID 2042988 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[CH:2].I[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1>>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=2)[CH:17]=1

Participants

3

Reactant 2

HCID 707143-IodopyridineHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 54757836HCID 54757836, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (102 mg, 0.54 mmol) and 3-iodopyridine (122 mg, 0.60 mmol) according to the general procedure IC to give 27 mg (43% b.r.s.m.) of an orange brown solid after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:3). Rf: 0.09 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 8.76-7.75 (m, 1H), 7.54-7.52 (m, 1H), 7.81-7.77 (m, 1H), 7.48-7.45 (m, 2H), 7.29-7.25 (m, 1H), 7.22-7.19 (m, 2H), 3.67 (s, 3H), 3.00-2.95 (t, 2H, J=7.8 Hz), 2.67-2.62 (t, 2H, J=7.8 Hz); 13CNMR (CDCl3) δ 173.0, 152.2, 148.4, 141.5, 138.3, 131.8, 128.4, 123.0, 120.5, 120.4, 92.5, 85.7, 51.6, 35.3, 30.8; EI-MS calcd for C17H15NO2 (M+): 265. found: 265.

Workup

  1. customto give 27 mg (43% b.r.s.m.) of an orange brown solid
  2. customafter purification by flash chromatography (SiO2, EtOAc/hexanes, 1:3)

Sources & evidence

ORD record
ord-28f444318cb24dffb58d18706e0faf5d
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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