Sodium Carbonate → HCID 178427348, 화합물

HRID 527081

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HRID 527081 반응식
[C:1]([O:5][C:6]([NH:8][C:9](=[N:26]C(=O)OC(C)(C)C)[NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18]2[C:23]([F:24])=[CH:22][N:21]=[C:20](Cl)[N:19]=2)[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:34][C:35]1[CH:36]=[C:37]2[C:43](B3OC(C)(C)C(C)(C)O3)=[CH:42][N:41]([S:53]([C:56]3[CH:61]=[CH:60][C:59]([CH3:62])=[CH:58][CH:57]=3)(=[O:55])=[O:54])[C:38]2=[N:39][CH:40]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:24][C:23]1[C:18]([NH:17][C@H:13]2[CH2:14][CH2:15][CH2:16][C@@H:11]([NH:10][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[NH:26])[CH2:12]2)=[N:19][C:20]([C:43]2[C:37]3[C:38](=[N:39][CH:40]=[C:35]([F:34])[CH:36]=3)[N:41]([S:53]([C:56]3[CH:61]=[CH:60][C:59]([CH3:62])=[CH:58][CH:57]=3)(=[O:54])=[O:55])[CH:42]=2)=[N:21][CH:22]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 672856905-fluoro-1-((4-methylphenyl)sulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 178454306HCID 178454306, 화합물

생성물 1

HCID 178427348HCID 178427348, 화합물

시약·촉매·용매 2

HCID 15220664Palladium--triphenylphosphane (1/1)촉매HCID 80711,2-Dimethoxyethane용매

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온도
120 °C

실험 절차

Degassed a solution of (Z)-tert-butyl (tert-butoxycarbonylamino) ((1R,3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexylamino)methylenecarbamate, 70b, (0.200 g, 0.411 mmol), 5-fluoro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine, 44a, (0.205 g, 0.493 mmol) and Na2CO3 (0.616 mL of 2M solution, 1.232 mmol) in dimethoxyethane (15 mL) for 30 min. To the mixture was added palladium triphenylphosphane (0.023 g, 0.021 mmol) and the reaction mixture was heated in a pressure tube at 120° C. for 45 min. The reaction mixture was filtered through a pad of celite and the filtrate concentrated in vacuo. Attempted purification of the resulting residue by silica gel chromatography (10% MeOH/CH2Cl2) yielded a mixture containing mostly desired product that was used without further purification: LCMS RT=2.30 (M+H) 641.02.

후처리

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customAttempted purification of the resulting residue by silica gel chromatography (10% MeOH/CH2Cl2)
  4. customyielded a mixture

출처 및 근거

ORD 기록
ord-d5f0b8e0275e494ea94050bdb7d0b2ae
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345708B2

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