Water → HCID 90020550, compound

HRID 2200185Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:12](=[NH:25])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>O1CCOCC1.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].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:19]1([C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:25][C:2]2[CH:3]=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Add 3-bromo-5-(trifluoromethyl)pyridine (600 mg, 2.67 mmol), benzophenone imine (701 mg, 4.0 mmol), Cs2CO3 (2.17 g, 6.68 mmol), BINAP (25 mg, 0.040 mmol), Pd2(dba)3 (24 mg, 0.027 mmol) in 1,4-dioxane (10 mL), stir at 110° C. for 16 hrs. Cool to room temperature, add water (100 mL), extract with EtOAc (15 mL×3), wash the combined organic layers with brine, dry over anhydrous Na2SO4, concentrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=6:94) affords the target compound (850 mg, 98%).

Workup

temperatureCool to room temperature
extractionextract with EtOAc (15 mL×3)
washwash the combined organic layers with brine
dry with materialdry over anhydrous Na2SO4
concentrationconcentrate under reduced pressure
customto give the crude product
customPurification by chromatography (silica gel, EtOAc:PE=6:94)

Sources & evidence

ORD record: ord-37b0df9789f64306950ea523754d7a57
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359338B2

Reaction notes

Loading…