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Potassium Phosphate, Tribasic → 5-(3-(6-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine

HRID 634171
ノート
印刷プレビュー

反応式

HRID 634171 の反応式
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[S:15][C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)=[N:13][N:12]=3)[CH:9]=2)[N:4]([S:26]([C:29]2[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH:3]=1.[Cl:36][C:37]1[N:42]=[C:41](B2OC(C)(C)C(C)(C)O2)[CH:40]=[CH:39][CH:38]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C(Cl)Cl.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>[Cl:36][C:37]1[N:42]=[C:41]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]4[S:15][C:14]([NH:16][CH2:17][C:18]5[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=5)=[N:13][N:12]=4)[CH:9]=3)[N:4]([S:26]([C:29]3[CH:30]=[CH:31][C:32]([CH3:33])=[CH:34][CH:35]=3)(=[O:28])=[O:27])[CH:3]=2)[CH:40]=[CH:39][CH:38]=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

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 177504912-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 683285925-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine

生成物 1

HCID 867251045-(3-(6-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine収率 90.3%

試薬・触媒・溶媒 3

HCID 11714597
Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)
触媒
HCID 6344Dichloromethane溶媒
HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
105 °C

実験手順

A glass microwave reaction vessel was charged with 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (300 mg, 0.487 mmol) and 6-chloropyridine-2-boronic acid pinacol ester (175 mg, 0.730 mmol) in p-dioxane/H2O (4:1, 5 mL) followed by bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (17.23 mg, 0.024 mmol) and potassium phosphate (310 mg, 1.460 mmol). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 105° C. for 30 min. The mixture was diluted with DCM and washed with H2O. The organic layer was dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 0-20% EtOAc in DCM) to give 5-(3-(6-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (265 mg, 0.440 mmol, 90%) as a yellow solid. MS (ESI, pos. ion) m/z: 602 (M+1); 1H NMR (400 MHz, CDCl3) δ ppm 8.73 (1H, d, J=1.4 Hz), 8.14 (1H, s), 8.05 (1H, d, J=8.8 Hz), 7.92 (1H, dd, J=8.7, 1.7 Hz), 7.81 (2H, d, J=8.2 Hz), 7.68-7.75 (1H, m), 7.59-7.66 (1H, m), 7.33 (2H, d, J=8.6 Hz), 7.24 (2H, d, J=3.7 Hz), 6.90 (2H, d, J=8.8 Hz), 4.54 (2H, s), 3.81 (3H, s), 2.35 (3H, s).

後処理

  1. customA glass microwave reaction vessel
  2. washwashed with H2O
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel chromatography (eluting with 0-20% EtOAc in DCM)

出典と根拠

ORDレコード
ord-6b06da4bdc6f4beb909436b187509671
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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