Propargyl bromide → HCID 22050251, compound

HRID 1832038Notes

Reaction equation

[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[NH:9][C:8](=[O:13])[CH:7]=1.[CH2:19](Br)[C:20]#[CH:21]>>[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([CH2:21][C:20]#[CH:19])[C:8](=[O:13])[CH:7]=1

Participants

Reactant 2

HCID 7842Propargyl bromide

HCID 22051141HCID 22051141, compound

Product 1

HCID 22050251HCID 22050251, compoundYield 44.9%

Procedure

The title compound was prepared by alkylation of 4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one (2.5 g, 10 mmol) with propargyl bromide (1.3 ml, 11.0 mmol) as described above to give 1.3 g (44%) of the desired product. 1H-NMR (DMSOd6/300 MHz) δ 7.60 (app q, J=8.4 hz, 1H), 7.35-7.27 (m, 1H); 7.16-7.10 (m, 1H); 5.94 (d, J=2.1 Hz, 1H), 5.88 (d, J=3.0 Hz, 1H), 5.03 (s, 2H), 4.76 (d, J=2.4, Hz, 2H), 3,31 (s, 3H), 3.24 (t, J=2.4 Hz, 1H), 2.39 (s, 3H); ES-HRMS m/z 290.0994 (M+H calcd for C16H14F2NO2=290.0993).

Sources & evidence

ORD record: ord-517c68d54107413a8f7e6bce8bd0ea0e
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067540B2

Reaction notes

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