Potassium Phosphate, Tribasic → 5-(3-Bromo-1,2,4-thiadiazol-5-yl)-2-(2-methylpropyl)benzonitrile

HRID 1942632노트

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HRID 1942632 반응식
[CH3:1][CH:2]([CH3:21])[CH2:3][C:4]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:5]=1[C:6]#[N:7].[Br:22][C:23]1[N:27]=[C:26](Cl)[S:25][N:24]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:22][C:23]1[N:27]=[C:26]([C:9]2[CH:10]=[CH:11][C:4]([CH2:3][CH:2]([CH3:1])[CH3:21])=[C:5]([CH:8]=2)[C:6]#[N:7])[S:25][N:24]=1

참가 물질

8

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 27250533-Bromo-5-chloro-1,2,4-thiadiazoleHCID 51358167Benzonitrile, 2-(2-methylpropyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

생성물 1

HCID 669817585-(3-Bromo-1,2,4-thiadiazol-5-yl)-2-(2-methylpropyl)benzonitrile수율 88.5%

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a solution of 2-(2-methylpropyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (D59) (500 mg), 3-bromo-5-chloro-1,2,4-thiadiazole (699 mg) and tripotassium phosphate (1116 mg) in N,N-dimethylformamide (DMF) (6 mL) and water (1.500 mL) stirred under nitrogen was added PdCl2(dppf) (154 mg). The reaction mixture was sealed and heated under microwave at 80° C. for 1 h. After cooling the reaction, the mixture was diluted with ethyl acetate, the organic phase was washed with water, dried and concentrated, the residue was purified by column chromatography to afford 5-(3-bromo-1,2,4-thiadiazol-5-yl)-2-(2-methylpropyl)benzonitrile (D60) (500 mg). δH (CDCl3, 400 MHz): 0.99 (6H, d), 2.04 (1H, m), 2.80 (2H, d), 7.46 (1H, d), 8.05 (1H, dd), 8.22 (1H, d). MS (ES): C13H12BrN3S requires 321. found 322.0 (M+H+).

후처리

  1. customThe reaction mixture was sealed
  2. temperatureAfter cooling
  3. customthe reaction
  4. washthe organic phase was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-8ec5e75776284223949eebea1236fcc3
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389508B2

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