N-Methylaniline → HCID 57831042, compound

HRID 600392Notes

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.[CH3:25][NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:13][C:12]([CH3:15])([CH3:14])[C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([N:26]([CH3:25])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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: 120 °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 (0.053 g, 0.129 mmol), N-methylaniline (0.021 mL, 0.19 mmol), Pd2(dba)3 (0.012 g, 0.013 mmol), BINAP (0.012 g, 0.019 mmol) and cesium carbonate (0.084 g, 0.258 mmol) in 2 mL of toluene was stirred at 120° C. in a microwave for 1 h, then at 150° C. in a microwave for 1 h, then at 180° C. in a microwave for 1 h, then concentrated to a residue. Column chromatography (0→30% EtOAc/hexanes) afforded 0.021 g (37%) of 2,2-dimethyl-1-[2-(methyl-phenyl-amino)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one as a yellow oil.

Workup

waitat 150° C. in a microwave for 1 h
waitat 180° C. in a microwave for 1 h
concentrationconcentrated to a residue

Sources & evidence

ORD record: ord-a3a8dfdfd9284221a656d38b812d7057
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902197B2

Reaction notes

Loading…