Dichloromethane → HCID 178492096, 화합물

HRID 2388987노트

반응식

HRID 2388987 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-661d2f9a80f842a98c344a6f14262f53
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268994B2

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