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Cesium carbonate → 6-bromo-N-(4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridin-2-yl)-4-methylpyridin-2-amine

HRID 2402378
ノート
印刷プレビュー

反応式

HRID 2402378 の反応式
Br[C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[N:10][N:11]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[Br:22][C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([NH2:30])[N:24]=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+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:22][C:23]1[N:24]=[C:25]([NH:30][C:2]2[CH:7]=[C:6]([C:8]3[N:9]=[N:10][N:11]([CH2:13][C:14]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=4)[CH:12]=3)[CH:5]=[CH:4][N:3]=2)[CH:26]=[C:27]([CH3:29])[CH:28]=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

6

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 221765076-Bromo-4-methylpyridin-2-amineHCID 866808002-bromo-4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridine

生成物 1

HCID 866808016-bromo-N-(4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridin-2-yl)-4-methylpyridin-2-amine収率 59.3%

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

反応条件

温度
100 °C

実験手順

To a flask was added 2-bromo-4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridine (329 mg, 0.953 mmol), 2-bromo-4-methyl-6-aminopyridine (178 mg, 0.953 mmol), Pd(OAc)2 (21.4 mg, 0.095 mmol), Xantphos (83 mg, 0.143 mmol), and Cs2CO3 (621 mg, 1.91 mmol), and the mixture was vacuum-purged with argon 3 times. Degassed 1,4-Dioxane (3.8 mL) was added and the reaction was heated to 100° C. for 30 min. after which time the reaction was cooled and diluted with EtOAc (20 mL). The reaction was filtered then dry loaded onto silica and purified by silica gel chromatography using a gradient solvent system of 30-60% EtOAc/Hexanes. Concentration of the product-containing fractions yielded 6-bromo-N-(4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridin-2-yl)-4-methylpyridin-2-amine (255 mg, 59%) as a tan solid. MS ESI calcd for C21H19BrN6O [M+H]+ 451, found 451.

後処理

  1. customthe mixture was vacuum-purged with argon 3 times
  2. additionDegassed 1,4-Dioxane (3.8 mL) was added
  3. temperaturewas cooled
  4. additiondiluted with EtOAc (20 mL)
  5. filtrationThe reaction was filtered
  6. customthen dry
  7. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-e15f7cd93ecc4f449b59e1b9c96fdac9
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08796310B2

反応ノート

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