HCID 71279793, compound → N-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(1-(2-(dimethylamino)ethyl)-6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246675Notes

Reaction equation

HRID 246675 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]([NH:13][C:14]([CH3:25])([CH3:24])[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[O:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:26][N:27]([CH3:53])[CH2:28][CH2:29][N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([CH3:39])[CH:37]=2)[C:32]([Sn](CCCC)(CCCC)CCCC)=[N:31]1>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I>[Si:17]([O:16][CH2:15][C:14]([NH:13][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:32]3[C:33]4[C:38](=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=4)[N:30]([CH2:29][CH2:28][N:27]([CH3:26])[CH3:53])[N:31]=3)[N:3]=2)[NH:8][CH:9]=1)=[O:12])([CH3:25])[CH3:24])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

7

Reactant 2

HCID 71279793HCID 71279793, compoundHCID 866779982-Bromo-N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Product 1

HCID 71279590N-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(1-(2-(dimethylamino)ethyl)-6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-bromo-N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (210 mg, 0.5 mmol) and N,N-dimethyl-2-(6-methyl-3-(tributylstannyl)-1H-indazol-1-yl)ethanamine (1.4 g, 2.85 mmol) with tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol), copper iodide (10 mg, 0.52 mmol) in 15 mL of dry DMF was heated to 85° C. overnight under N2. The reaction mixture was cooled to room temperature, diluted with 50 mL of water, extracted with dichloromethane (8×50 mL), combined organics dried with sodium sulfate and concentrated. The crude product was used into the next step without further purification. LCMS: (M+H)+=550.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with dichloromethane (8×50 mL)
  3. dry with materialcombined organics dried with sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was used into the next step without further purification

Sources & evidence

ORD record
ord-9ead19d4747846a2bec1f55a1a7c9cc2
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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