Triethylamine → (E)-4-(2-methyl-benzothiazol-6-yl)-but-3-enoic acid methyl ester

HRID 1469652

Reaction equation

I[C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[S:8][C:4]=2[CH:3]=1.[CH3:12][O:13][C:14](=[O:18])[CH2:15][CH:16]=[CH2:17].C(N(CC)CC)C>C(O[Pd]OC(=O)C)(=O)C>[CH3:12][O:13][C:14](=[O:18])[CH2:15]/[CH:16]=[CH:17]/[C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[S:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 6-iodo-2-methylbenzo[d]thiazole (275 mg, 1 mmol), but-3-enoic acid methyl ester (100 mg, 1.2 mmol), diacetoxypalladium (22 mg, 0.1 mmol) and triethylamine (304 mg, 3 mmol) MeCN (8 mL) is heated in a microwave apparatus at 130° C. for 30 minutes. The solvent is removed under reduce pressure and the residue is purified by flash chromatography (heptane:EtOAc, 2:1) to give (E)-4-(2-methyl-benzothiazol-6-yl)-but-3-enoic acid methyl ester. MS 248.3 (M+1).

Workup

customThe solvent is removed
customthe residue is purified by flash chromatography (heptane:EtOAc, 2:1)

Sources & evidence

ORD record: ord-53a6c4fa039b49bf999bd75a0eb18c20
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006249B2

Linked notes

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