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Cesium carbonate → Methyl 4-(8-(3-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate

HRID 57764
ノート
印刷プレビュー

反応式

HRID 57764 の反応式
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([N:15]=[C:16]([NH2:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.I[C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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>[F:20][C:2]([F:19])([F:1])[C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([N:15]=[C:16]([NH:18][C:22]4[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=4)[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=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 3

HCID 10796Cesium carbonateHCID 69273Methyl 4-iodobenzoateHCID 591990748-(3-Trifluoromethylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

生成物 1

HCID 44554495Methyl 4-(8-(3-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate収率 72.1%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate
触媒
HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A suspension of 8-(3-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (1.0 g, 3.6 mmol, 1 equiv), methyl 4-iodobenzoate (0.95 g, 3.6 mmol, 1.0 equiv), palladium (II) acetate (0.080 g, 0.36 mmol, 0.10 equiv), cesium carbonate (2.34 g, 7.18 mmol, 2.0 equiv), and Xantphos (0.10 g, 0.17 mmol, 0.047 equiv) in 1,4-dioxane (20 mL) was heated to 80° C. After 16 h, the reaction mixture was concentrated in vacuo, and the resulting residue was diluted with methanol and water. The solid was collected by filtration and rinsed sequentially with water, isopropanol, and hexanes to afford crude methyl 4-(8-(3-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate (1.07 g, 72%). LCMS (ESI) m/z: 413.0; 1H NMR (400 MHz, DMSO-d6) δ: 10.29 (s, 1H), 8.88 (m, 1H), 8.63 (s, 1H), 8.40 (m, 1H), 8.02 (m, 1H), 7.78-7.90 (m, 6H), 7.20 (m, 1H), 3.80 (s, 3H).

後処理

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionthe resulting residue was diluted with methanol and water
  3. filtrationThe solid was collected by filtration
  4. washrinsed sequentially with water, isopropanol, and hexanes

出典と根拠

ORDレコード
ord-75560ac2175a4fdda25280f337f9e548
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09434732B2

反応ノート

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