Tetrahydrofuran → N-(2-chloro-5-(2-(methylamino)benzo[d]thiazol-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

HRID 2077613ノート

反応式

HRID 2077613 の反応式
[CH3:1][NH:2][C:3]1[S:4][C:5]2[CH:11]=[C:10](B3OC(C)(C)C(C)(C)O3)[CH:9]=[CH:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:28]1[CH:29]=[C:30]([NH:35][S:36]([C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=2)(=[O:38])=[O:37])[C:31]([Cl:34])=[N:32][CH:33]=1.C1COCC1>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].O>[Cl:34][C:31]1[C:30]([NH:35][S:36]([C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=2)(=[O:38])=[O:37])=[CH:29][C:28]([C:10]2[CH:9]=[CH:8][C:6]3[N:7]=[C:3]([NH:2][CH3:1])[S:4][C:5]=3[CH:11]=2)=[CH:33][N:32]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 53363354N-(5-bromo-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamideHCID 58279591N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-amine

生成物 1

HCID 57585117N-(2-chloro-5-(2-(methylamino)benzo[d]thiazol-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide収率 21.3%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒

実験手順

To a microwave vial equipped with a stirbar and charged with N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-amine (0.22 g, 0.75 mmol), cesium carbonate (0.67 g, 2.1 mmol), PdCl2(dppf)*DCM (0.10 g, 0.12 mmol), N-(5-bromo-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide (0.250 g, 0.68 mmol) was added THF (3 ml). Then water (0.5 ml) was added into the mixture. The vial was capped and then placed into a CEM Microwave for 10 minutes at 100° C., while 100 watts of energy was supplied via Powermax® (Simultaneous heating while cooling technology). The progress of the reaction was monitored by LC/MS, which showed desired material in the mixture. The organic layer was extracted from the microwave vial by pipet and then diluted the organic with acetonitrile (15 ml) and TFA (0.1 ml). The crude was purified by reverse-phase HPLC. This gave N-(2-chloro-5-(2-(methylamino)benzo[d]thiazol-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (0.065 g, 21% yield) as a yellow crystalline solid. MS (ESI pos. ion) m/z: 449 (MH+). Calc'd exact mass for C19H14ClFN4O2S2: 448. 1H NMR (400 MHz, DMSO-d6): 2.97 (d, J=3.51 Hz, 3H), 7.42 (t, J=8.78 Hz, 2H), 7.46-7.53 (m, 2H), 7.81 (dd, J=8.53, 5.02 Hz, 2H), 7.94 (s, 1H), 8.03 (s, 1H), 8.13 (d, J=4.02 Hz, 1H), 8.54 (s, 1H), 10.45 (s, 1H).

後処理

  1. customTo a microwave vial equipped with a stirbar
  2. customThe vial was capped
  3. temperaturewas supplied via Powermax® (Simultaneous heating while cooling technology)
  4. extractionThe organic layer was extracted from the microwave vial by pipet
  5. additiondiluted the organic with acetonitrile (15 ml) and TFA (0.1 ml)
  6. customThe crude was purified by reverse-phase HPLC

出典と根拠

ORDレコード
ord-1d114f40017d4af3baef12bd3b2050db
出典データセット
uspto-grants-2011_04
特許番号
US07928140B2

反応ノート

読み込み中…