N-bromobutanimide → HCID 22050081, compound

HRID 1867050Notes

Reaction equation

[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([CH2:13][C:14]#[CH:15])[C:8](=[O:16])[CH:7]=1.C1C(=O)N([Br:29])C(=O)C1>>[Br:29][C:7]1[C:8](=[O:16])[N:9]([CH2:13][C:14]#[CH:15])[C:10]([CH3:12])=[CH:11][C:6]=1[O:5][CH2:4][C:3]1[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:2]=1[F:1]

Participants

Reactant 2

HCID 67184N-bromobutanimide

HCID 22050251HCID 22050251, compound

Product 1

HCID 22050081HCID 22050081, compoundYield 57%

Procedure

Bromination of 4-[(2,4-difluorobenzyl)oxy]-6-methyl-1-prop-2-ynylpyridin-2(1H)-one (500 mg, 1.67 mmol) with NBS (300 mg, 1.67 mmol) was carried out in the manner described above to give 350 mg (57%) of the desired compound. 1H-NMR (DMSO-d6/300 MHz) δ 7.67 (app q, J=9.0 hz, 1H), 7.36 (app dt, J=10.5, 2.4 hz, 1H); 7.23-7.16 (m, 1H); 6.60 (s, 1H), 5.29 (s, 2H), 4.90 (d, J=2.4, Hz, 1H), 3.35 (s, 3H), 3.32 (s, 1H), 2.53 (s, 3H); ES-HRMS m/z 368.0107 (M+H calcd for C11H13BrF2NO2=368.0098).

Sources & evidence

ORD record: ord-9cc4e66df07b4d19a5ab48f948e84a2b
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629363B2

Reaction notes

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