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Potassium Phosphate, Tribasic → 2-(3-(2,4-difluorophenyl)-1-tosyl-1H-indol-5-yl)-5-(methylsulfonyl)-1,3,4-thiadiazole

HRID 634163
ノート
印刷プレビュー

反応式

HRID 634163 の反応式
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1B1OC(C)(C)C(C)(C)O1.I[C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:36]3[S:37][C:38]([S:41]([CH3:44])(=[O:43])=[O:42])=[N:39][N:40]=3)[CH:34]=2)[N:29]([S:45]([C:48]2[CH:54]=[CH:53][C:51]([CH3:52])=[CH:50][CH:49]=2)(=[O:47])=[O:46])[CH:28]=1>CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl.CC(O)C.O>[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:36]3[S:37][C:38]([S:41]([CH3:44])(=[O:43])=[O:42])=[N:39][N:40]=3)[CH:34]=2)[N:29]([S:45]([C:48]2[CH:54]=[CH:53][C:51]([CH3:52])=[CH:50][CH:49]=2)(=[O:47])=[O:46])[CH:28]=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 62657Potassium Phosphate, TribasicHCID 162176522-(2,4-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 683282122-(3-iodo-1-tosyl-1H-indol-5-yl)-5-(methylsulfonyl)-1,3,4-thiadiazole

生成物 1

HCID 683286122-(3-(2,4-difluorophenyl)-1-tosyl-1H-indol-5-yl)-5-(methylsulfonyl)-1,3,4-thiadiazole収率 37.5%

試薬・触媒・溶媒 2

HCID 11714597
Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)
触媒
HCID 21889133Propan-2-ol--water (1/1)溶媒

反応条件

温度
80 °C

実験手順

A mixture of potassium phosphate tribasic (1.309 g, 6.17 mmol, Aldrich), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.044 g, 0.062 mmol, Aldrich), 2,4-difluorophenylboronic acid pinacol ester (0.740 g, 3.08 mmol, Aldrich), 2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-(methylsulfonyl)-1,3,4-thiadiazole (1.15 g, 2.056 mmol), and IPA/H2O (70%, 10 mL) was heated at 80° C. for 2 h. The mixture was partially concentrated to remove most IPA, and the aq. layer was extracted with DCM. The aq. layer was acidified with 2M HCl and extracted again with DCM. The combined DCM fractions were evaporated and purified by prep HPLC (50-95% AcCN/H2O/0.1% TFA) to give 2-(3-(2,4-difluorophenyl)-1-tosyl-1H-indol-5-yl)-5-(methylsulfonyl)-1,3,4-thiadiazole (0.42 g, 0.770 mmol, 37.4%) as a light yellow solid. MS (ESI, pos. ion) m/z 546 (M+1).

後処理

  1. concentrationThe mixture was partially concentrated
  2. customto remove most IPA
  3. extractionthe aq. layer was extracted with DCM
  4. extractionextracted again with DCM
  5. customThe combined DCM fractions were evaporated
  6. custompurified by prep HPLC (50-95% AcCN/H2O/0.1% TFA)

出典と根拠

ORDレコード
ord-865d605dfff24052b33096189df91e88
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321756B2

反応ノート

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