Sodium Carbonate → N-(2-Chloro-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide

HRID 1963795ノート

反応式

HRID 1963795 の反応式
Br[C:2]1[CH:3]=[C:4]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1.[O:21]1[CH2:26][CH2:25][O:24][C:23]2[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][C:22]1=2.C(=O)([O-])[O-].[Na+].[Na+]>CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:5]1[C:4]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:3][C:2]([C:28]2[CH:29]=[CH:30][C:22]3[O:21][CH2:26][CH2:25][O:24][C:23]=3[CH:27]=2)=[CH:7][N:6]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2776178(2,3-Dihydro-1,4-benzodioxin-6-yl)boronic acidHCID 51355175HCID 51355175、化合物

生成物 1

HCID 58229519N-(2-Chloro-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒

反応条件

温度
85 °C

実験手順

A 15 mL sealed pressure tube was charged with N-(5-bromo-2-chloropyridin-3-yl)-4-methoxybenzenesulfonamide (190 mg, 0.503 mmol), 2,3-dihydrobenzo[b][1,4]dioxin-6-ylboronic acid (100 mg, 0.553 mmol) in EtOH (1.5 ml). Pd(PPh3)4 (29 mg, 0.025 mmol) was added, followed by sodium carbonate (2M, 0.629 mL). The tube was purged with argon, backfilled with argon, sealed and stirred at 85° C. for 1.5 hours. The crude was partitioned between water and methylene chloride and extracted with methylene chloride (3×, 10 ml). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo. The solid was purified by ISCO with a 20-50% gradient of EtOAc in hexanes to afford desired product. MS (ESI pos. ion) m/z calcd for C20H12ClN2O5S: 432.8; found 433.3 1H NMR (400 MHz, DMSO-d6) δ ppm 3.83 (s, 3 H), 4.30 (s, 4 H), 6.99 (d, J=8.3 Hz, 1 H), 7.06-7.15 (m, 4 H), 7.61-7.72 (m, 2 H), 7.78 (d, J=2.3 Hz, 1 H), 8.47 (s, 1 H), 10.21 (s, 1 H).

後処理

  1. customA 15 mL sealed pressure tube
  2. customThe tube was purged with argon
  3. customsealed
  4. customThe crude was partitioned between water and methylene chloride
  5. extractionextracted with methylene chloride (3×, 10 ml)
  6. dry with materialThe combined organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe solid was purified by ISCO with a 20-50% gradient of EtOAc in hexanes

出典と根拠

ORDレコード
ord-a7b5ef18add048eab39cd255800af012
出典データセット
uspto-grants-2013_04
特許番号
US08415376B2

反応ノート

読み込み中…