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Sodium Carbonate → HCID 57585089、化合物

HRID 2077616
ノート
印刷プレビュー

反応式

HRID 2077616 の反応式
Br[C:2]1[CH:12]=[CH:11][C:5]2[N:6]=[C:7]([S:9][CH3:10])[S:8][C:4]=2[CH:3]=1.[Cl:13][C:14]1[C:19]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:18][C:17](B2CC(C)(C)C(C)(C)C2)=[CH:16][N:15]=1.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:13][C:14]1[C:19]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:18][C:17]([C:2]2[CH:12]=[CH:11][C:5]3[N:6]=[C:7]([S:9][CH3:10])[S:8][C:4]=3[CH:3]=2)=[CH:16][N:15]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 179535146-Bromo-2-(methylsulfanyl)-1,3-benzothiazoleHCID 86628003HCID 86628003、化合物

生成物 1

HCID 57585089HCID 57585089、化合物収率 11%

試薬・触媒・溶媒 2

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

反応条件

温度
90 °C

実験手順

In a 15 mL sealed-pressure tube was added 6-bromo-2-(methylthio)benzo[d]thiazole (60 mg, 0.231 mmol), N-(2-chloro-5-(3,3,4,4-tetramethylborolan-1-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide (137 mg, 0.323 mmol), sodium carbonate (2M) (73 mg, 0.692 mmol) and 8 mol % Pd(PPh3)4 in 2.0 ml of EtOH. The tube was purged with argon for 10 minutes, back-filled with argon, sealed and placed in a pre heated oil bath at 90° C. for 2 hours. Analysis of an aliquot by LCMS shows a small amount of desired product (RT=2.66 min.), exhaustion of boronic ester starting material, remaining aryl bromide starting material, and an unidentified byproduct with mw 315. Added an additional 20 mg of Pd(PPh3)4 and 60 mg of boronic ester starting material. Continued to heat at 90° C. for two more hours. No additional conversion by LCMS. Stopped reaction and cooled to ambient temperature. Concentrated down in vacuo. Crude taken up in equal parts MeOH and DMSO, filtered and purified by Gilson RPHPLC with a 20-95% gradient of ACN in water with 0.1% TFA as a modifier. Following basification with saturated sodium bicarb and extraction with 10 ml DCM (2×), organic layer was dried over Na2SO4, filtered and concentrated in vacuo to afford N-(2-chloro-5-(2-(methylthio)benzo[d]thiazol-6-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide (12 mg, 11% yield). MS (ESI pos. ion) m/z: 478 (MH+).

後処理

  1. customThe tube was purged with argon for 10 minutes
  2. additionback-filled with argon
  3. customsealed
  4. additionAdded an additional 20 mg of Pd(PPh3)4 and 60 mg of boronic ester starting material
  5. temperatureto heat at 90° C. for two more hours
  6. customStopped reaction
  7. temperaturecooled to ambient temperature
  8. concentrationConcentrated down in vacuo
  9. filtrationfiltered
  10. custompurified by Gilson RPHPLC with a 20-95% gradient of ACN in water with 0.1% TFA as a modifier
  11. extractionwith saturated sodium bicarb and extraction with 10 ml DCM (2×), organic layer
  12. dry with materialwas dried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e13ab72193c74b9a9631541530b239b6
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07928140B2

反応ノート

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