Potassium Carbonate → HCID 73505782、化合物

HRID 1478585ノート

反応式

HRID 1478585 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][N:15]3[C:19]4=[N:20][C:21]([C:24]5[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=5)=[CH:22][N:23]=[C:18]4[N:17]=[N:16]3)[CH2:9]2)=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1.[F:42][C:43]1[CH:55]=[C:54](B2OC(C)(C)C(C)(C)O2)[CH:53]=[CH:52][C:44]=1[CH2:45][N:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>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].O>[F:42][C:43]1[CH:55]=[C:54]([C:2]2[CH:3]=[N:4][C:5]([N:8]3[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][N:15]4[C:19]5=[N:20][C:21]([C:24]6[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=6)=[CH:22][N:23]=[C:18]5[N:17]=[N:16]4)[CH2:9]3)=[N:6][CH:7]=2)[CH:53]=[CH:52][C:44]=1[CH2:45][N:46]1[CH2:47][CH2:48][O:49][CH2:50][CH2:51]1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 438110633-Fluoro-4-(N-morpholinomethyl)phenylboronic acid, pinacol esterHCID 73507291HCID 73507291、化合物

生成物 1

HCID 73505782HCID 73505782、化合物収率 111.2%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒

実験手順

In a pressure tube reactor, (S)-4-(5-bromopyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine (40 mg, 0.08 mmol) was added, and then K2CO3 (36 mg, 0.26 mmol) was added. Pd(dppf)2Cl2 (4 mg, 0.004 mmol) was further added, and 1,4-dioxane (2 mL) and water (0.5 mL) were added. 4-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzyl)morpholine (42 mg, 0.13 mmol) was added, and then stirred at room temperature under nitrogen gas for 10 minutes, followed by stirring at 85° C. for 2 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate and water, and the extra water was removed by sodium sulfate, followed by concentration under reduced pressure. Column chromatography using 50% ethyl acetate/hexane gave (S)-4-(5-(3-fluoro-4-(morpholinomethyl)phenyl)pyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine (51 mg, 0.089 mmol) with a yield of 46%.

後処理

  1. stirringby stirring at 85° C. for 2 hours
  2. extractionthe organic layer was extracted with ethyl acetate and water
  3. customthe extra water was removed by sodium sulfate
  4. concentrationfollowed by concentration under reduced pressure

出典と根拠

ORDレコード
ord-d996c77cc5ff44f3aef92d92c31f5fec
出典データセット
uspto-grants-2016_08
特許番号
US09403831B2

反応ノート

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