Dichloromethane → N-tert-Butyl-3'-fluoro-4'-[1,2,4]triazolo[4,3-a]pyridin-7-ylbiphenyl-2-sulfonamide

HRID 1523953ノート

反応式

HRID 1523953 の反応式
[C:1]([NH:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18](B3OC(C)(C)C(C)(C)O3)=[C:17]([F:30])[CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:32]1[CH:37]=[CH:36][N:35]2[CH:38]=[N:39][N:40]=[C:34]2[CH:33]=1.C(Cl)Cl>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]>[C:1]([NH:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18]([C:32]3[CH:37]=[CH:36][N:35]4[CH:38]=[N:39][N:40]=[C:34]4[CH:33]=3)=[C:17]([F:30])[CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:7])=[O:8])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 231159667-Bromo-[1,2,4]triazolo[4,3-a]pyridineHCID 90313401N-(tert-butyl)-3'-fluoro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-sulfonamide

生成物 1

HCID 90313645N-tert-Butyl-3'-fluoro-4'-[1,2,4]triazolo[4,3-a]pyridin-7-ylbiphenyl-2-sulfonamide収率 70.7%

試薬・触媒・溶媒 1

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

反応条件

温度
80 °C

実験手順

To a 20 mL vial were added N-(tert-butyl)-3′-fluoro-4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-2-sulfonamide (45 mg, 0.10 mmol), 7-bromo-[1,2,4]triazolo[4,3-a]pyridine (21 mg, 0.10 mmol) K2CO3 (29 mg, 0.21 mmol), Pd(dppf)Cl2.CH2Cl2 (4 mg, 0.005 mmol), and a stir bar. The vial was sealed with a teflon lined cap and the vial sparged with N2. The vial was then charged with freshly sparged DMSO (2 mL) and stirred for 16 hours at 80° Celsius. The reaction mixture was then cooled to rt, filtered, and purified by HPLC to give the title compound (30 mg, 53%). MS (ESI): mass calcd. for C22H21FN4O2S, 424.14; m/z found, 425.1 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 9.40 (s, 1H), 8.79 (s, 1H), 8.20-8.11 (m, 2H), 7.77 (m, 1H), 7.70-7.57 (m, 3H), 7.47-7.38 (m, 3H), 1.10 (s, 9H).

後処理

  1. customlined cap
  2. customthe vial sparged with N2
  3. additionThe vial was then charged with freshly sparged DMSO (2 mL)
  4. temperatureThe reaction mixture was then cooled to rt
  5. filtrationfiltered
  6. custompurified by HPLC

出典と根拠

ORDレコード
ord-ffd4634f4862426ab58277147e4e2284
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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