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Methanol → HCID 46203075、化合物

HRID 1662270
ノート
印刷プレビュー

反応式

HRID 1662270 の反応式
Br[C:2]1[CH:3]=[C:4]([C:10]2([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:18]3[C:13](=[C:14]([F:19])[CH:15]=[CH:16][CH:17]=3)[C:12]([NH2:20])=[N:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[N:31]1[CH:36]=[C:35](B(O)O)[CH:34]=[N:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+].CO>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[C:12]([NH2:20])=[N:11][C:10]2([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([C:35]2[CH:36]=[N:31][CH:32]=[N:33][CH:34]=2)[CH:3]=1)[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=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 887MethanolHCID 11430Potassium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 58579532HCID 58579532、化合物

生成物 1

HCID 46203075HCID 46203075、化合物収率 43.3%

試薬・触媒・溶媒 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

1-(3-Bromo-4-methoxyphenyl)-4-fluoro-1-(2-(trifluoromethyl)pyridin-4-yl)-1H-isoindol-3-amine (1.5 g, 3.12 mmol), pyrimidin-5-ylboronic acid (0.542 g, 4.37 mmol), [1,1′-bis (diphenylphosphino)ferrocene]palladium(II) chloride (0.128 g, 0.16 mmol) and aqueous potassium carbonate (2M, 4.69 mL, 9.37 mmol) were dissolved in DMF (14 mL). The resulting mixture was heated to 150° C. for 20 mins by microwaves. Methanol (20 mL) was added and the mixture concentrated in vacuo. Dichloromethane (40 mL), water (20 mL) and brine (5 mL) were added and the organic phase separated and evaporated directly on silica. The crude product was purified by gradient column chromatography (40 g silica column eluted with 0-10% [0.1M ammonia in methanol] in dichloromethane). The desired fractions were combined and evaporated to give 648 mg (43%) of the title compound.

後処理

  1. concentrationthe mixture concentrated in vacuo
  2. additionDichloromethane (40 mL), water (20 mL) and brine (5 mL) were added
  3. customthe organic phase separated
  4. customevaporated directly on silica
  5. customThe crude product was purified by gradient column chromatography (40 g silica column eluted with 0-10% [0.1M ammonia in methanol] in dichloromethane)
  6. customevaporated

出典と根拠

ORDレコード
ord-234729235199446189614b145aa6713a
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08030500B2

反応ノート

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