Cesium carbonate → HCID 11288891, compound

HRID 1765094Notes

Reaction equation

Cl[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9](=[NH:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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.C1(C)C=CC=CC=1>[C:9](=[N:22][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 2-chloro-3-fluoropyridine (21.0 g, 0.16 mol), benzophenone imine (32.3 g, 0.18 mol), Cs2CO3 (73.0 g, 0.23 mol), BINAP (5.96 g, 9.6 mmol), palladium(II) acetate (1.45 g, 6.4 mmol) and toluene (370 ml) were heated to 95° C. for 42 h, then cooled, filtered and the residue extracted with further toluene (2×210 ml). The filtrate was washed with 0.5 N hydrochloric acid (200 ml) and saturated aqueous NaHCO3 (200 ml), dried over anhydrous MgSO4 and concentrated in vacuo, affording crude benzhydrylidene(3-fluoropyridin-2-yl)amine as a brown oil (49.4 g) which was used directly without further purification: m/z (ES+) 277 (100%, [MH]+)

Workup

temperaturecooled
filtrationfiltered
extractionthe residue extracted with further toluene (2×210 ml)
washThe filtrate was washed with 0.5 N hydrochloric acid (200 ml) and saturated aqueous NaHCO3 (200 ml)
dry with materialdried over anhydrous MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d1246d1dd321423b86378206d16dd800
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07226926B2

Reaction notes

Loading…