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

HRID 634139
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인쇄 미리보기

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HRID 634139 반응식
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.[F: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>[F: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
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참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 426145762-Fluoro-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

생성물 1

HCID 683283935-(3-(6-fluoropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine수율 88%

시약·촉매·용매 3

HCID 11714597
Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)
촉매
HCID 6344Dichloromethane용매
HCID 218864351,4-Dioxane--water (1/1)용매

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온도
105 °C

실험 절차

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 (500 mg, 0.811 mmol) and 6-fluoropyridine-2-boronic acid pinacol ester (226 mg, 1.014 mmol) in p-dioxane/H2O (4:1, 7.5 mL) followed by potassium phosphate (430 mg, 2.028 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (28.7 mg, 0.041 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 5-15% EtOAc in DCM with 1% MeOH) to give 5-(3-(6-fluoropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (418 mg, 0.714 mmol, 88%) as a yellow solid. MS (ESI, pos. ion) m/z: 378 (M+1).

후처리

  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 5-15% EtOAc in DCM with 1% MeOH)

출처 및 근거

ORD 기록
ord-910bbcd04d29450abd971e6f440c5f10
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321756B2

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