4-Iodo-2-methyl-1,3-thiazole → 7-Chloro-5-fluoro-2-(4-(2-methylthiazol-4-yl)but-3-ynyl)benzo[d]oxazole

HRID 334579Notes

Reaction equation

HRID 334579 reaction equation
I[C:2]1[N:3]=[C:4]([CH3:7])[S:5][CH:6]=1.[CH2:8]([C:12]1[O:13][C:14]2[C:20]([Cl:21])=[CH:19][C:18]([F:22])=[CH:17][C:15]=2[N:16]=1)[CH2:9][C:10]#[CH:11]>>[Cl:21][C:20]1[C:14]2[O:13][C:12]([CH2:8][CH2:9][C:10]#[C:11][C:2]3[N:3]=[C:4]([CH3:7])[S:5][CH:6]=3)=[N:16][C:15]=2[CH:17]=[C:18]([F:22])[CH:19]=1

Participants

3

Reactant 2

HCID 537067904-Iodo-2-methyl-1,3-thiazoleHCID 860867442-(But-3-ynyl)-7-chloro-5-fluorobenzo[d]oxazole

Product 1

HCID 116167467-Chloro-5-fluoro-2-(4-(2-methylthiazol-4-yl)but-3-ynyl)benzo[d]oxazoleYield 55.1%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 4-iodo-2-methylthiazole (200 mg, 0.89 mmol) and 2-(but-3-ynyl)-7-chloro-5-fluorobenzo[d]oxazole (199 mg, 0.89 mmol). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 85:15) to yield 157 mg (0.49 mmol, 55%) of 7-chloro-5-fluoro-2-(4-(2-methylthiazol-4-yl)but-3-ynyl)benzo[d]oxazole as a yellow solid.

Workup

  1. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 85:15)

Sources & evidence

ORD record
ord-e9cfd103645748798fde2961421b9d18
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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