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Potassium Phosphate, Tribasic → 5-[3-(2-Ethyl-3-formylphenyl)-1,2,4-thiadiazol-5-yl]-2-(2-methylpropyl)benzonitrile

HRID 1942635
ノート
印刷プレビュー

反応式

HRID 1942635 の反応式
Br[C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])=[C:11]([CH:14]=2)[C:12]#[N:13])[S:4][N:3]=1.[CH2:19]([C:21]1[C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=[O:24])[CH3:20].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C.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>[CH2:19]([C:21]1[C:22]([CH:23]=[O:24])=[CH:25][CH:26]=[CH:27][C:28]=1[C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])=[C:11]([CH:14]=2)[C:12]#[N:13])[S:4][N:3]=1)[CH3:20]
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

8

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 584940852-Ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehydeHCID 669817585-(3-Bromo-1,2,4-thiadiazol-5-yl)-2-(2-methylpropyl)benzonitrile

生成物 1

HCID 584941545-[3-(2-Ethyl-3-formylphenyl)-1,2,4-thiadiazol-5-yl]-2-(2-methylpropyl)benzonitrile収率 89.2%

試薬・触媒・溶媒 4

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

To a solution of 5-(3-bromo-1,2,4-thiadiazol-5-yl)-2-(2-methylpropyl)benzonitrile (D60) (500 mg), 2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (D5) (424 mg) and tripotassium phosphate (988 mg) in N,N-dimethylformamide (DMF) (4 mL) and water (1 mL) stirred under nitrogen was added Pd(Ph3P)4 (179 mg). The mixture was sealed and heated under microwave at 120° C. for 15 min. After cooling the reaction, the mixture was diluted with ethyl acetate, washed with water, dried over sodium sulphate, concentrated and purified by column chromatography to give 5-[3-(2-ethyl-3-formylphenyl)-1,2,4-thiadiazol-5-yl]-2-(2-methylpropyl)benzonitrile (D63) (520 mg). δH (CDCl3, 400 MHz): 1.00 (6H, d), 1.37 (3H, t), 2.81 (2H, d), 3.38 (2H, q), 4.11 (1H, m), 7.48 (2H, m), 8.02 (1H, d), 8.14 (2H, m), 8.30 (1H, d), 10.48 (1H, s). MS (ES): C22H21N3OS requires 375. found 376.1 (M+H+).

後処理

  1. customThe mixture was sealed
  2. temperatureAfter cooling
  3. customthe reaction
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. custompurified by column chromatography

出典と根拠

ORDレコード
ord-6f19b4ef56ae469bafee26999165ef95
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08389508B2

反応ノート

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