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

HRID 1523903노트

반응식

HRID 1523903 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

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

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온도
80 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-bfb1a4ac2170486dbce5bba17217744b
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079866B2

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