2-Methoxyethane-1-sulfonyl chloride → N-(3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-methoxyethanesulfonamide

HRID 1052566Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:8]=1)[NH2:5].[CH3:18][O:19][CH2:20][CH2:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:5][S:22]([CH2:21][CH2:20][O:19][CH3:18])(=[O:24])=[O:23])[CH:6]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:8]=1

Participants

Conditions

Temperature: 45 °C

Procedure

3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (250 mg, 1.05 mmol) was treated with 2-methoxyethanesulfonyl chloride (326 mg, 2.06 mmol) and 1 ml pyridine as a solvent according to the method described in Preparation 15b but stirring at 45° C. during 3 h. The residue was purified using SP1® Purification System (0% to 100% hexane-ethyl acetate) to obtain 80 mg (17% yield, 81% purity) of the title compound.

Workup

customThe residue was purified
customSP1® Purification System (0% to 100% hexane-ethyl acetate)

Sources & evidence

ORD record: ord-67d65dfb55e741f3a0ed456586fdfdc7
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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