Dichloromethane → HCID 59633050, compound

HRID 2369025Notes

Reaction equation

[Br:1][C:2]1[S:6][C:5]([C:7]2[N:11](C)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:13](Cl)Cl>>[Br:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][N:10]([CH3:13])[N:11]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 6344Dichloromethane2×

HCID 59631729HCID 59631729, compound

Product 1

HCID 59633050HCID 59633050, compound

Procedure

To a stirred solution of 1-(5-bromothiophen-2-yl)-3-dimethylaminopropenone (0.70 g, 2.7 mmol) in EtOH (15 mL) was added methylhydrazine (0.16 mL, 3.0 mmol) and then acetic acid (0.45 mL, 8.0 mmol). The resulting mixture was heated at reflux for 2 h, allowed to cool to ambient temperature and then concentrated under reduced pressure. The residue was diluted with DCM (50 mL), washed with H2O and brine, then dried (Na2SO4), concentrated and purified by chromatography (silica, DCM) to yield the title compound 10a (0.21 g) as a white solid and regioisomer, 5-(5-bromothiophen-2-yl)-1-methyl-1H-pyrazole, 11a (035 g) as a pale yellow solid. 10a: Rf 0.42 (DCM); 1H-NMR (CD2Cl2): δ 7.36 (1H, d), 7.01 (2H, m), 6.41 (1H, d), 3.87 (3H, s); 11a: Rf 0.19 (DCM); 1H-NMR (CD2Cl2): δ 7.42 (1H, d), 7.10 (1H, d), 6.94 (1H, m), 6.36 (1H, d), 3.92 (3H, s).

Sources & evidence

ORD record: ord-a5eb698bcad04b319e4a5e35dfee8d33
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703805B2

Reaction notes

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