Sodium Carbonate → HCID 131734996、化合物

HRID 923662ノート

反応式

HRID 923662 の反応式
[C:1]([O:5][C:6](=[O:34])[N:7]([CH:9]([C:11](=[O:33])[NH:12][C:13]1[CH:18]=[C:17](Br)[C:16]([Cl:20])=[C:15]([C:21]#[C:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[N:14]=1)[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:35][N:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][C:43]=2B(O)O)[CH:38]=[N:37]1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[C:1]([O:5][C:6](=[O:34])[N:7]([C@H:9]([C:11](=[O:33])[NH:12][C:13]1[CH:18]=[C:17]([C:43]2[CH:42]=[CH:41][CH:40]=[C:39]3[C:44]=2[N:36]([CH3:35])[N:37]=[CH:38]3)[C:16]([Cl:20])=[C:15]([C:21]#[C:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[N:14]=1)[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 44118216(1-Methyl-1H-indazol-7-yl)boronic acidHCID 123381143tert-butyl-N-{1-[(4-bromo-5-chloro-6-{2-[tris(propan-2-yl)silyl]ethynyl}-pyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate

生成物 1

HCID 131734996HCID 131734996、化合物

試薬・触媒・溶媒 3

HCID 24290Palladium Chloride触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 962Water溶媒2 回

反応条件

温度
100 °C

実験手順

1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (20 mg, 0.03 mmol) is added to a mixture of tert-butyl-N-{1-[(4-bromo-5-chloro-6-{2-[tris(propan-2-yl)silyl]ethynyl}-pyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate C2 (82 mg, 0.14 mmol), (1-methyl-1H-indazol-7-yl)boronic acid (24 mg, 0.14 mmol), Na2CO3 (44 mg, 0.42 mmol), dioxane (0.8 ml) and water (0.2 ml) under argon atmosphere and stirred at 100° C. for 4 h. The mixture is diluted with water (10 ml) and extracted with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 25 mg (28%). HPLC-MS: M+H=624; tR=1.94 min (METHOD—1).

後処理

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by RP HPLC

出典と根拠

ORDレコード
ord-1c681887f67341188b475b9338c8185f
出典データセット
uspto-grants-2016_03
特許番号
US09278978B2

反応ノート

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