Cesium carbonate → HCID 86642312, compound

HRID 906001Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[C:10]([Cl: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]([Cl: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-chloro-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine (1.31 g, 3.61 mmol), benzhydrylideneamine (0.67 mL, 3.97 mmol), Cs2CO3 (2.35 g, 7.22 mmol), Pd(OAc)2 (81 mg, 0.361 mmol) and BINAP (225 mg, 0.361 mmol) were dissolved in THF (36 mL) and heated at 100° C. overnight, cooled to RT, partitioned between EtOAc and brine. The organic layer was dried (MgSO4), filtered, concentrated, and purified by SiO2 chromatography (150 g SiO2, hexanes/EtOAc 0-25% EtOAc) to give 992 mg of benzhydrylidene-[7-chloro-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-amine as a yellow liquid (59% yield).

Workup

temperaturecooled to RT
custompartitioned between EtOAc and brine
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
custompurified by SiO2 chromatography (150 g SiO2, hexanes/EtOAc 0-25% EtOAc)

Sources & evidence

ORD record: ord-6e985f83b64c43f2b63aa7d2d9b71661
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012974B2

Reaction notes

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