Cesium carbonate → HCID 86642310, compound

HRID 905995Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[C:10]([CH3:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]2=[N:6][CH:7]=1.[C:20](=[NH:33])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+].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>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:20](=[N:33][C:2]1[N:3]=[C:4]2[C:10]([CH3:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]2=[N:6][CH:7]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Bromo-7-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine (0.346 g, 1.01 mmol), benzhydrylideneamine (0.19 mL, 1.11 mmol), Cs2CO3 (658 mg, 2.02 mmol), Pd(OAc)2 (23 mg, 0.101 mmol) and BINAP (63 mg, 0.101 mmol) were dissolved in THF (10 mL) and heated at 100° C. for 63 hr, cooled to RT, partitioned between EtOAc and brine. The organic layer was dried (MgSO4), filtered, concentrated, and purified by SiO2 chromatography (40 g SiO2, hexanes/EtOAc 0-35% EtOAc) to give 158 mg of benzhydrylidene-[7-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-amine as a yellow liquid (20% yield).

Workup

temperaturecooled to RT
custompartitioned between EtOAc and brine
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
custompurified by SiO2 chromatography (40 g SiO2, hexanes/EtOAc 0-35% EtOAc)

Sources & evidence

ORD record: ord-aec36ac08e174424a4dd335aad3d97d1
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012974B2

Reaction notes

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