HCID 58303321, compound → 2-Imidazo[1,2-a]pyridin-3-yl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide

HRID 246239Notes

Reaction equation

HRID 246239 reaction equation
[C:1]([CH:3]1[CH2:6][N:5]([C:7](=[O:31])[C@H:8]([NH:10][C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19](Br)[N:20]=3)[N:15]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:14]=2)=[O:12])[CH3:9])[CH2:4]1)#[N:2].C([Sn](CCCC)(CCCC)[C:37]1[N:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]2=[N:39][CH:38]=1)CCC>CN(C=O)C.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>[C:1]([CH:3]1[CH2:6][N:5]([C:7](=[O:31])[C@H:8]([NH:10][C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:37]4[N:41]5[CH:42]=[CH:43][CH:44]=[CH:45][C:40]5=[N:39][CH:38]=4)[N:20]=3)[N:15]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:14]=2)=[O:12])[CH3:9])[CH2:4]1)#[N:2]

Participants

5

Reactant 2

HCID 58303321HCID 58303321, compoundHCID 584386122-Bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]amide

Product 1

HCID 712857092-Imidazo[1,2-a]pyridin-3-yl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

2-Bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]amide (110 mg, 0.22 mmol) was combined with 3-tributylstannanyl-imidazo[1,2-a]pyridine (159 mg, 0.39 mmol) in DMF that had been sparged with nitrogen for 10 min. To this was added tetrakis(triphenylphosphine)palladium(0) (25 mg, 0.022 mmol) and the mixture heated to 70-80° C. for 3 h. All solvent was removed by high vacuum evaporation and the product purified by silica gel chromatography to give 2-imidazo[1,2-a]pyridin-3-yl-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide. LCMS: (M+H)+=544.

Workup

  1. customhad been sparged with nitrogen for 10 min
  2. customAll solvent was removed by high vacuum evaporation
  3. customthe product purified by silica gel chromatography

Sources & evidence

ORD record
ord-c4e9f740df4141bea7427e34eaff5591
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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