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Potassium Carbonate → HCID 90403372、化合物

HRID 1049380
ノート
印刷プレビュー

反応式

HRID 1049380 の反応式
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16]([NH:18][C:19](=[O:25])[C:20]([O:23][CH3:24])([CH3:22])[CH3:21])=[O:17])=[N:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH2:26]([N:29]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[N:30]1)[CH:27]=[CH2:28].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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>[CH2:26]([N:29]1[CH:33]=[C:32]([C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16]([NH:18][C:19](=[O:25])[C:20]([O:23][CH3:24])([CH3:22])[CH3:21])=[O:17])=[N:13][CH:14]=3)[CH:5]=[CH:4][N:3]=2)[CH:31]=[N:30]1)[CH:27]=[CH2:28]
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 11430Potassium CarbonateHCID 583546341-(Prop-2-en-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 90403342HCID 90403342、化合物

生成物 1

HCID 90403372HCID 90403372、化合物収率 15.3%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒
HCID 962
Water
溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A mixture of Example C5 (0.12 g, 0.33 mmol), 1-allyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.085 g, 0.36 mmol) and K2CO3 (0.14 g, 0.99 mmol) in dioxane (4 mL) and H2O (1 mL) was sparged with Ar, treated with Pd(PPh3)4 (0.040 g, 0.034 mmol), sparged again with Ar and heated at 90° C. overnight. The mixture was cooled to RT, treated with satd. NaHCO3, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via reverse phase silica gel chromatography (MeCN/H2O (0.1% TFA)) to obtain N-((5-((2-(1-allyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)-2-methoxy-2-methylpropanamide (22 mg, 14.6%). 1H NMR (400 MHz, DMSO-d6): δ 10.83 (s, 1H), 10.21 (br s, 1H), 8.41 (d, J=5.8 Hz, 1H), 8.33 (s, 1H), 8.28 (d, J=2.9 Hz, 1H), 8.05 (s, 1H), 8.03 (br s, 1H), 7.76 (dd, J=9.0, 2.9 Hz, 1H), 7.31 (d, J=2.4 Hz, 1H), 6.77 (d, J=5.7 Hz, 1H), 6.02 (m, 1H), 5.21 (m, 1H), 5.13 (m, 1H), 4.77 (d, J=5.8 Hz, 2H), 3.21 (s, 3H), 1.36 (s, 6H); MS (ESI) m/z: 437.2 (M+H+).

後処理

  1. customsparged again with Ar
  2. temperatureThe mixture was cooled to RT
  3. additiontreated with satd
  4. extractionNaHCO3, extracted with EtOAc (3×)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. custompurified via reverse phase silica gel chromatography (MeCN/H2O (0.1% TFA))

出典と根拠

ORDレコード
ord-0514a5f4eef8471a8b72c89ec07e44f3
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09382228B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート