Sodium Carbonate → HCID 131734996, 화합물

HRID 923662노트

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HRID 923662 반응식
[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]

참가 물질

8

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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

생성물 1

HCID 131734996HCID 131734996, 화합물

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 962Water용매2회

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1c681887f67341188b475b9338c8185f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278978B2

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