1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 89761916、化合物

温度

100 °C

A mixture of N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (Intermediate M; 500 mg, 1.19 mmol), 1-bromo-2-(methoxymethoxy)benzene (1.2 g, 5.98 mmol), Pd2(dba)3 (109 mg, 0.119 mmol, GLR), Xantphos (138 mg, 0.23 mmol, GLR) and sodium-tert-butoxide (229 mg, 2.39 mmol) in toluene (15 mL) was degassed with nitrogen for 10 minutes. The reaction mixture was heated at 100° C. for 1 h under microwave. After completion, the reaction mixture was diluted with water (15 mL) and extracted with ethyl acetate (3×15 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by combiflash column chromatography (column size: 12 g; elution: 0-20% ethyl acetate in hexane) to yield N-(4-methoxybenzyl)-4-(2-(methoxymethoxy)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (600 mg, 90.7%). MS (ESI, positive ion) m/z; 554.1 (M+1).

1. customwas degassed with nitrogen for 10 minutes
2. additionAfter completion, the reaction mixture was diluted with water (15 mL)
3. extractionextracted with ethyl acetate (3×15 mL)
4. dry with materialThe organic layer was dried over sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customto obtain the crude material which
7. customwas purified by combiflash column chromatography (column size: 12 g; elution: 0-20% ethyl acetate in hexane)

ORDレコード

ord-417da32ff6f84a93bcb40308123c0343

出典データセット

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09346798B2