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Cesium carbonate → HCID 69671629、化合物

HRID 626752
ノート
印刷プレビュー

反応式

HRID 626752 の反応式
Cl[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[CH:5]=[CH:4][N:3]=1.[CH:19]1([C:22]2[N:27]=[CH:26][N:25]=[C:24]([NH2:28])[CH:23]=2)[CH2:21][CH2:20]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:19]1([C:22]2[N:27]=[CH:26][N:25]=[C:24]([NH:28][C:2]3[C:7]4=[CH:8][N:9]([C:11]5[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=5[Cl:18])[N:10]=[C:6]4[CH:5]=[CH:4][N:3]=3)[CH:23]=2)[CH2:21][CH2:20]1
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 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 450804916-Cyclopropylpyrimidin-4-amineHCID 866970364-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

生成物 1

HCID 69671629HCID 69671629、化合物収率 43.2%

試薬・触媒・溶媒 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

A mixture of 4-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (52 mg, 0.175 mmol), 6-cyclopropylpyrimidin-4-ylamine (26 mg, 0.193 mmol), Pd2(dba)3 (8 mg, 0.0088 mmol), Xantphos (10.1 mg, 0.0175 mmol) and cesium carbonate (114 mg, 0.35 mmol) in dioxane (1.5 mL) was de-gassed and purged with nitrogen and the reaction mixture was heated at 120° C. in the microwave for 1 hour. The resultant mixture was filtered and washed with dioxane. The filtrate was concentrated under reduced pressure and the resultant residue was purified by silica gel flash chromatography (0-100% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (30 mg, 43% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.56 (d, J=0.9 Hz, 1H), 8.94 (d, J=1.0 Hz, 1H), 8.05 (d, J=7.3 Hz, 1H), 7.87-7.83 (m, 2H), 7.79-7.74 (m, 1H), 7.62 (dd, J=7.3, 0.9 Hz, 1H), 7.39 (s, 1H), 2.34-2.26 (m, 1H), 1.19-1.12 (m, 4H). LCMS (Method B): RT=3.17 min, m/z: 397 [M+H+].

後処理

  1. customwas de-gassed
  2. custompurged with nitrogen
  3. filtrationThe resultant mixture was filtered
  4. washwashed with dioxane
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resultant residue was purified by silica gel flash chromatography (0-100% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-22ab8f4b18924161aa1054980232ee96
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309240B2

反応ノート

読み込み中…

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