3-(Methylcarbamoyl)benzeneboronic acid → HCID 59593137、化合物

HRID 2262247ノート

反応式

HRID 2262247 の反応式
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9](I)=[C:8]([CH3:12])[C:6]=2[N:7]=1.[CH3:19][NH:20][C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].CC1(C)C(C)(C)OB([C:40]2[CH:48]=[CH:47][CH:46]=[C:45]3[C:41]=2[CH:42]=[N:43][NH:44]3)O1>C([O-])([O-])=O.[Na+].[Na+].C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:44]1[C:45]2[C:41](=[C:40]([C:2]3[N:3]=[C:4]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)[C:5]4[S:10][C:9]([C:27]5[CH:28]=[C:23]([CH:24]=[CH:25][CH:26]=5)[C:21]([NH:20][CH3:19])=[O:22])=[C:8]([CH3:12])[C:6]=4[N:7]=3)[CH:48]=[CH:47][CH:46]=2)[CH:42]=[N:43]1

参加物

7

反応物 3

HCID 27735243-(Methylcarbamoyl)benzeneboronic acidHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 595928802-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine

生成物 1

HCID 59593137HCID 59593137、化合物

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒2 回HCID 6342Acetonitrile溶媒2 回HCID 10340Sodium Carbonate溶媒2 回

反応条件

温度
150 °C

実験手順

2-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine from Example 12 (0.1 g, 0.3 mmol), 3-(N-Methylaminocarbonyl)benzeneboronic acid (50 mg, 0.3 mmol), and bis(triphenylphosphine)palladium(II) dichloride (9 mg, 13 μmol) in 1 M aqueous Na2CO3 (0.5 mL) and acetonitrile (0.5 mL) were heated to 100° C. in a sealed microwave reactor for 10 min. Upon completion, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 (122 mg, 0.5 mmol), bis(triphenylphosphine)palladium(II) dichloride (9 mg, 13 μmol), 1 M aqueous Na2CO3 (1 mL), and acetonitrile (1 mL) were added into the same pot. The reaction mixture was heated to 150° C. in a sealed microwave reactor for 20 min. The mixture was extracted with EtOAc and CH2Cl2. The combined organics were concentrated to yield 358 after reverse phase HPLC purification (2 mg). MS (Q1) 485 (M)+

後処理

  1. extractionThe mixture was extracted with EtOAc and CH2Cl2
  2. concentrationThe combined organics were concentrated

出典と根拠

ORDレコード
ord-adde83436b4240458779ef2716f72e18
出典データセット
uspto-grants-2010_12
特許番号
US07846929B2

反応ノート

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