Aniline → HCID 57831046, compound

HRID 600391Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O.[NH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CS(C)=O.[Cu]I>[CH3:13][C:12]([CH3:15])([CH3:14])[C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([NH:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:3]=2)[N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:9]=1)=[O:16]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1-[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.206 g, 0.50 mmol), potassium carbonate (0.152 g, 1.10 mmol), copper (I) iodide (0.014 g, 0.075 mmol), proline (0.017 g, 0.15 mmol) and aniline (0.46 mL, 5 mmol) in 1 mL of dimethylsulfoxide was stirred at 90° C. for 5 d, then allowed to cool. The mixture was partitioned between 50 mL of ethyl acetate and 30 mL of water, and the organic layer was washed with 30 mL of a sat. aq. NaCl solution, dried over MgSO4, and concentrated to a residue. Column chromatography (0→45% EtOAc/hexanes) afforded 0.102 g (48%) of 2,2-dimethyl-1-[2-phenylamino-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one as a pale orange solid.

Workup

temperatureto cool
customThe mixture was partitioned between 50 mL of ethyl acetate and 30 mL of water
washthe organic layer was washed with 30 mL of a sat. aq. NaCl solution
dry with materialdried over MgSO4
concentrationconcentrated to a residue

Sources & evidence

ORD record: ord-eba23af21ae34dc58f3b7bc5d9cc11d7
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902197B2

Reaction notes

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