4-amino-N-methylbenzene-1-sulfonamide → 4-(6-chloro-4-pyrrolidin-1-yl-pyridin-2-ylamino)-N-methyl-benzenesulfonamide

HRID 1437749ノート

反応式

HRID 1437749 の反応式
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([Cl:13])[N:3]=1.CC(C)([O-])C.[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[NH2:66][C:67]1[CH:72]=[CH:71][C:70]([S:73]([NH:76][CH3:77])(=[O:75])=[O:74])=[CH:69][CH:68]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:13][C:4]1[N:3]=[C:2]([NH:66][C:67]2[CH:72]=[CH:71][C:70]([S:73]([NH:76][CH3:77])(=[O:75])=[O:74])=[CH:69][CH:68]=2)[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=1

参加物

8

反応物 4

HCID 743684-amino-N-methylbenzene-1-sulfonamideHCID 634876Binap, (A+-)-HCID 11644208HCID 11644208、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 116392174-(6-chloro-4-pyrrolidin-1-yl-pyridin-2-ylamino)-N-methyl-benzenesulfonamide収率 24.6%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

To a solution of 2,6-dichloro-4-pyrrolidino-pyridine (0.350 g, 1.62 mmol) in toluene (6 mL) were added potassium tert-butoxide (0.132 g, 1.18 mmol), palladium(II)-acetate (36.40 mg, 0.160 mmol), BINAP (32 mg, 0.514 mmol) and 4-amino-N-methyl-benzenesulfonamide (227 mg, 1.22 mmol) in a 10 mL reaction vessel. This reaction mixture was subjected the microwave irradiation, in which the microwave power was 250 W, to attain a reaction temperature of 150° C. After this reaction proceeded for 30 min, water (150 mL) was added to the reaction mixture and the reaction product was extracted with ethyl acetate. The organic layer was dried over sodium sulphate, filtered, and the filtrate concentrated under vacuum. The product was purified through column chromatography using 230-400 mesh silica gel (elution 20:80 acetone:petroleum ether) to afford the desired compound as a light brown solid (110 mg, yield 19%).

後処理

  1. customin a 10 mL reaction vessel
  2. customthe microwave irradiation
  3. customa reaction temperature of 150° C
  4. extractionthe reaction product was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe product was purified through column chromatography

出典と根拠

ORDレコード
ord-c614b00504ad44569f7b6db84973d737
出典データセット
uspto-grants-2009_11
特許番号
US07622486B2

反応ノート

読み込み中…