5-Bromothiazole → HCID 54757623, compound

HRID 2043014Notes

Reaction equation

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

Participants

Reactant 2

HCID 5460595-Bromothiazole

HCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 54757623HCID 54757623, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (95 mg, 0.50 mmol) and 5-bromothiazole (50 μL, 0.56 mmol) according to the general procedure IF. After concentration the residue was hydrolyzed according to the general procedure II to give 28 mg (21%) of a white solid after purification by flash chromatography (SiO2, EtOAc [with 1.25% AcOH]:PE, 1:2): Rf=0.12 ([EtOAc with 1.25% AcOH]:PE, 1:2); 1H NMR (DMSO-d6) δ 12.14 (s, 1H), 9.16 (d, J=0.6 Hz, 1H), 8.20 (d, J=0.6 Hz, 1H), 7.49 (d, J=8.2 Hz, 3H), 7.31 (d, J=8.3 Hz, 3H), 2.86 (t, J=7.5 Hz, 3H), 2.56 (t, J=7.6 Hz, 3H); 13C NMR (DMSO-d6) δ 173.5, 155.7, 147.2, 142.6, 131.2, 128.7, 118.8, 118.0, 96.0, 78.4, 34.6, 30.1; ESI-MS calcd for C14H11NO2S (M+Na+) 280.0403. found 280.0400.

Workup

concentrationAfter concentration the residue

Sources & evidence

ORD record: ord-8839f7395c9b4b5a9473a5bd98c2e713
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

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