Dichloromethane → HCID 178492096, compound

HRID 1865650Notes

Reaction equation

HRID 1865650 reaction equation
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]

Participants

8

Reactant 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

Product 1

HCID 178492096HCID 178492096, compoundYield 38.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-c66b7681e27f4cd283790efd5ed54f10
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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