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Structure of 254887-17-7

Chemical Structure| 254887-17-7

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Product Details of [ 254887-17-7 ]

CAS No. :254887-17-7
Formula : C8H9BrO2S
M.W : 249.12
SMILES Code : O=S(C1=CC(Br)=CC=C1C)(C)=O
MDL No. :MFCD04037925
InChI Key :SRYXZVWRMOFVCO-UHFFFAOYSA-N
Pubchem ID :2761056

Safety of [ 254887-17-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 254887-17-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 254887-17-7 ]

[ 254887-17-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 254887-17-7 ]
  • [ 885069-14-7 ]
  • [ 1192831-42-7 ]
YieldReaction ConditionsOperation in experiment
23% With cesium fluoride;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; at 90℃; A mixture of lambda/-[6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,3- benzothiazol-2-yl]acetamide (1 eq), the halogenated derivative (1.5 to 2 eq), cesium fluoride (3 to 5 eq) and bis(thphenylphosphine)palladium(ll) chloride(0.05 to 0.15 eq) was prepared in dioxane/water (ratio 2:1 to 3:1 , typical concentration from 0.05 to 0.5M). The resulting mixture was heated at 900C for 30 min to 15 hours typically. Depending of the solubility of the final product, the same work-ups as described in Method A were applied. The title compound was prepared following procedure described in Method B (work-up C) starting from 4-bromo-1 -methyl-2-(methylsulfonyl)benzene. The title compound (14) was obtained as a pale orange powder (13 mg, 23%).HPLC, Rt: 3.7 min (purity: 95.3%). UPLC/MS, M+(ESI): 361.2, M-(ESI): 359.2. 1H-NMR (DMSO-de): delta 12.43 (s, 1 H), 8.36 (d, J=1.7 Hz, 1 H), 8.18 (d, J=1.9 Hz, 1 H), 7.97 (dd, J=1.9, 8.0 Hz, 1 H), 7.84 (d, J=8.5 Hz, 1 H), 7.76 (dd, J=1.7, 8.5 Hz, 1 H), 7.57 (d, J=8.0 Hz, 1 H), 3.29 (s, 3H), 2.68 (s, 3H), 2.22 (s, 3H).
With cesium fluoride;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; at 90℃; Method B: Suzuki cross-coupling reaction (Conditions B) A mixture of Lambda/-[6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,3-benzothiazol-2- yl]acetamide (1 eq), the halogenated derivative (1.5 to 2 eq), cesium fluoride (3 to 5 eq) and bis(triphenylphosphine)palladium(ll) chloride (0.05 to 0.15 eq) was prepared in dioxane/water (ratio 2:1 to 3:1 , typical concentration from 0.05 to 0.5M). The resulting mixture was heated at 900C for 30 min to 15 hours typically. Depending of the solubility of the final product, the same work-ups as described in Method A were applied.; Example 14: Formation of Lambda/-{6-[4-methyl-3-(methylsulfonyl)phenyl]-1 ,3- benzothiazol-2-yl}acetamide (14)The title compound was prepared following procedure described in Method B (workup C) starting from 4-bromo-1-methyl-2-(methylsulfonyl)benzene. The title compound (14) was obtained as a pale orange powder. HPLC, Rt: 3.7 min (purity: 95.3%).UPLC/MS, M+(ESI): 361.2, M-(ESI): 359.2. 1H-NMR (DMSOd6): delta 12.43 (s, 1 H), 8.36 (d, J=1.7 Hz, 1 H), 8.18 (d, J=1.9 Hz, 1 H), 7.97 (dd, J=1.9, 8.0 Hz, 1 H), 7.84 (d, J=8.5 Hz, 1 H), 7.76 (dd, J=1.7, 8.5 Hz, 1 H), 7.57 (d, J=8.0 Hz, 1 H), 3.29 (s, 3H), 2.68 (s, 3H), 2.22 (s, 3H).
 

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