Dichloromethane → HCID 178492096, 화합물

HRID 1865650노트

반응식

HRID 1865650 반응식
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][N:12]=3)=[N:9][N:8](COC(=O)C(C)(C)C)[C:5]2=[N:6][CH:7]=1.[NH2:27][C:28]1[CH:38]=[CH:37][C:36](B2OC(C)(C)C(C)(C)O2)=[CH:35][C:29]=1[C:30]([N:32]([CH3:34])[CH3:33])=[O:31].ClCCl.C(=O)(O)[O-].[Na+]>O1CCCC1.C(#N)C.O>[NH2:27][C:28]1[CH:38]=[CH:37][C:36]([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][N:12]=4)=[N:9][NH:8][C:5]3=[N:6][CH:7]=2)=[CH:35][C:29]=1[C:30]([N:32]([CH3:34])[CH3:33])=[O:31]

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 574162382-amino-N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 686631372,2-Dimethyl-propionic acid 5-bromo-3-(3-methoxy-pyridin-2-yl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester

생성물 1

HCID 178492096HCID 178492096, 화합물수율 38.8%

시약·촉매·용매 3

HCID 962Water용매2회HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

실험 절차

2,2-Dimethyl-propionic acid 5-bromo-3-(3-methoxy-pyridin-2-yl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester (570 mg, 1.36 mmol), 2-amino-N,N-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (570 mg, 1.96 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex in dichloromethane (1:1, 111 mg, 0.136 mmol), tetrahydrofuran (3 ml), acetonitrile (6 ml), water (3 ml), and saturated sodium bicarbonate (3 ml) were combined and irradiated in a microwave reactor for 20 minutes at 120° C. Water was added to the reaction mixture, and this was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography (0-100% [10% methanol in ethyl acetate] in hexanes) to give 205 mg (31%) 2-amino-5-[3-(3-methoxy-pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzamide. MS: m/z 503.4 (M+H+).

후처리

  1. customirradiated in a microwave reactor for 20 minutes at 120° C
  2. extractionthis was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (0-100% [10% methanol in ethyl acetate] in hexanes)

출처 및 근거

ORD 기록
ord-c66b7681e27f4cd283790efd5ed54f10
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07626021B2

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