Cesium carbonate → N-(2,4-dimethylphenyl)-3,5-difluoro-N-isobutyl-4-vinylbenzenesulfonamide

HRID 1487062ノート

反応式

HRID 1487062 の反応式
[B-](F)(F)(F)[CH:2]=[CH2:3].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:28]1[C:33]([F:34])=[CH:32][C:31]([S:35]([N:38]([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][C:44]=2[CH3:50])[CH2:39][CH:40]([CH3:42])[CH3:41])(=[O:37])=[O:36])=[CH:30][C:29]=1[F:51].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.ClCCl.O.[Pd](Cl)Cl>[CH3:50][C:44]1[CH:45]=[C:46]([CH3:49])[CH:47]=[CH:48][C:43]=1[N:38]([CH2:39][CH:40]([CH3:42])[CH3:41])[S:35]([C:31]1[CH:32]=[C:33]([F:34])[C:28]([CH:2]=[CH2:3])=[C:29]([F:51])[CH:30]=1)(=[O:37])=[O:36]

参加物

9

反応物 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 23679353Potassium vinyltrifluoroborate2 回HCID 898759904-bromo-N-(2,4-dimethylphenyl)-3,5-difluoro-N-isobutylbenzenesulfonamide

生成物 1

HCID 89875754N-(2,4-dimethylphenyl)-3,5-difluoro-N-isobutyl-4-vinylbenzenesulfonamide

試薬・触媒・溶媒 4

HCID 24290Palladium Chloride触媒HCID 962Water溶媒3 回HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
140 °C

実験手順

To a vial was added potassium trifluoro(vinyl)borate (0.744 g, 5.55 mmol), triphenylphosphine (0.073 g, 0.278 mmol), 4-bromo-N-(2,4-dimethylphenyl)-3,5-difluoro-N-isobutylbenzenesulfonamide (2 g, 4.63 mmol) suspension in tetrahydrofuran (THF) (22 mL), cesium carbonate (4.52 g, 13.88 mmol), water (2.200 mL) and palladium(II) chloride (0.016 g, 0.093 mmol). The mixture was divided evenly between two microwave vials and the vessels then sealed and heated by microwaves (Biotage Initiator) to 140° C. for 30 minutes. LCMS analysis showed some conversion, so additional 0.5 equivalent of potassium trifluoro(vinyl)borate was added to each reaction, along with extra water (2 mL) and THF (2 mL). The reactions were reheated by microwaves for a further 1 hour at 140° C. The reactions were then diluted with dichloromethane (5 mL) and water (2 mL), filtered through celite and dried using a hydrophobic frit. The organics were concentrated and purified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give two batches of the required product, 769 mg and 856 mg, as yellow oils. LCMS [LCMS2] Rt 1.60 min, m/z (ES+) 380 (M+H).

後処理

  1. customthe vessels then sealed
  2. filtrationfiltered through celite
  3. customdried
  4. concentrationThe organics were concentrated
  5. custompurified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient)
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-18a993b94ba04b60ba6fb44a910eab14
出典データセット
uspto-grants-2016_08
特許番号
US09428452B2

反応ノート

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