Dichloromethane → (S)-4'-(6-Aminopyridin-3-yl)-3'-fluoro-N-(1-hydroxypropan-2-yl)-[1,1'-biphenyl]-2-sulfonamide

HRID 1523903ノート

反応式

HRID 1523903 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][C:9]=2[F:17])=[CH:4][CH:3]=1.Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([NH:28][C@@H:29]([CH3:32])[CH2:30][OH:31])(=[O:27])=[O:26].C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CS(C)=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:19]3[C:20]([S:25]([NH:28][C@@H:29]([CH3:32])[CH2:30][OH:31])(=[O:27])=[O:26])=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:10][C:9]=2[F:17])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 65807018(S)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamideHCID 90313226(4-(6-Aminopyridin-3-yl)-3-fluorophenyl)boronic acid

生成物 1

HCID 90313516(S)-4'-(6-Aminopyridin-3-yl)-3'-fluoro-N-(1-hydroxypropan-2-yl)-[1,1'-biphenyl]-2-sulfonamide

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

A mixture of (4-(6-aminopyridin-3-yl)-3-fluorophenyl)boronic acid (100 mg, 0.43 mmol), (S)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamide (160 mg, 0.54 mmol), Pd(dppf)Cl2.CH2Cl2 (18 mg, 0.022 mmol), K2CO3 (340 mg, 2.4 mmol), and DMSO (3 mL) was sparged with nitrogen, then the reaction vessel was sealed and heated at 80° Celsius for 16 hours. The mixture was cooled to rt, then filtered, and subjected to HPLC purification to provide the title compound. MS (CI): mass calcd. for C20H20FN3O3S, 401.12; m/z found, 402.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 8.31-7.93 (m, 5H), 7.72-7.57 (m, 3H), 7.42-7.25 (m, 4H), 7.11-7.04 (d, J=9.2, 1H), 3.34-3.25 (s, 1H), 3.18-3.00 (m, 2H), 1.00-0.91 (d, J=6.5, 3H).

後処理

  1. customthe reaction vessel was sealed
  2. temperatureThe mixture was cooled to rt
  3. filtrationfiltered
  4. customsubjected to HPLC purification

出典と根拠

ORDレコード
ord-bfb1a4ac2170486dbce5bba17217744b
出典データセット
uspto-grants-2015_07
特許番号
US09079866B2

反応ノート

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