Methyl 1-(4-ethynyl-3-fluorobenzyl)azetidine-3-carboxylate → HCID 58415358, compound

HRID 2075239Notes

Reaction equation

HRID 2075239 reaction equation
[CH2:1]([C:8]1[N:13]=[C:12](I)[C:11]([OH:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([C:18]1[CH:32]=[CH:31][C:21]([CH2:22][N:23]2[CH2:26][CH:25]([C:27]([O:29][CH3:30])=[O:28])[CH2:24]2)=[CH:20][C:19]=1[F:33])#[CH:17]>>[CH2:1]([C:8]1[N:13]=[C:12]2[CH:17]=[C:16]([C:18]3[CH:32]=[CH:31][C:21]([CH2:22][N:23]4[CH2:26][CH:25]([C:27]([O:29][CH3:30])=[O:28])[CH2:24]4)=[CH:20][C:19]=3[F:33])[O:15][C:11]2=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 25254788Methyl 1-(4-ethynyl-3-fluorobenzyl)azetidine-3-carboxylateHCID 58415338HCID 58415338, compound

Product 1

HCID 58415358HCID 58415358, compound

Procedure

Synthesized according to Scheme B3 and general procedure G from 6-benzyl-2-iodopyridin-3-ol (0.500 g, 1.61 mmol) and methyl 1-(4-ethynyl-3-fluorobenzyl)azetidine-3-carboxylate (0.477 g, 1.93 mmol). 1H NMR (300 MHz, CDCl3) δ ppm 7.93 (t, J=7.9 Hz, 1H), 7.65 (d, J=8.5 Hz, 1H), 7.37 (d, J=3.1 Hz, 1H), 7.10-7.33 (m, 7H), 7.04 (d, J=8.5 Hz, 1H), 4.27 (s, 2H), 3.72 (s, 3H), 3.65 (s, 2H), 3.48-3.60 (m, 2H), 3.30-3.40 (m, 3H). MS (ESI) m/z: Calculated; 430.2 Observed: 431.1 (M++1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-7947a52443c24bd4a0e6c42df143e421
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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