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Diisopropylethylamine → 2-ethyl-4-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazole-5-carboxamide

HRID 881734
ノート
印刷プレビュー

反応式

HRID 881734 の反応式
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[O:3]1.[CH2:17]([C:19]1[O:20][C:21]([C:25](O)=[O:26])=[C:22]([CH3:24])[N:23]=1)[CH3:18].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.[Cl-].[Na+].O.O>[CH2:17]([C:19]1[O:20][C:21]([C:25]([NH:13][C:12]2[CH:14]=[CH:15][C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:10][CH:11]=2)=[O:26])=[C:22]([CH3:24])[N:23]=1)[CH3:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 138352982-Ethyl-4-methyl-1,3-oxazole-5-carboxylic acid

生成物 1

HCID 867008392-ethyl-4-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazole-5-carboxamide
収率 52.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (360 mg, 1.643 mmol) in anhydrous DMF (8.2 mL) was added 2-ethyl-4-methyloxazole-5-carboxylic acid (306 mg, 1.972 mmol), followed by DIPEA (0.86 mL, 4.93 mmol) and the mixture was stirred at room temperature for 10 minutes. HATU (750 mg, 1.972 mmol) was added and the mixture was stirred at room temperature for 16 hour. The mixture was taken up in 1:1 mixture of brine and water (40 mL) and extracted with EtOAc (60 mL). The organic portion was dried over sodium sulfate, filtered and concentrated to afford a brown oil, which was purified by flash column chromatography to afford the title compound (305 mg, 52% yield) as a white solid. LC/MS, ESI-MS (+): 357.1, RT: 1.35 (Condition E).

後処理

  1. stirringthe mixture was stirred at room temperature for 16 hour
  2. extractionextracted with EtOAc (60 mL)
  3. dry with materialThe organic portion was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a brown oil, which
  7. customwas purified by flash column chromatography

出典と根拠

ORDレコード
ord-176d063d63844eac8fbeb4ca21546df7
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08993619B2

反応ノート

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