Benzophenone imine → 2-(2-Fluoroethoxy)aniline
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH2:10][F:11].CC([O-])(C)C.[Na+].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(=[NH:77])(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1>[F:11][CH2:10][CH2:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:77]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
To a solution of the product of Example 126, Step 1 (800 mg, 3.65, mmol) in deoxygenated toluene (15 mL) was added NaOtBu (498 mg, 5.2 mmol), BINAP (364 mg, 0.58 mmol) Pd2(dba)3 (217 mg, 0.24 mmol) and benzophenone imine (0.8 mL, 4.7 mmol). The reaction mixture was heated at 120° C. for 3 h. The crude mixture was then washed with DCM and the aqueous layer was made basic with sat. NaHCO3. The aqueous layer was extracted with DCM and the combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography on silica gel (0-5% MeOH in DCM) to afford the title compound (566 mg, 90%). MS (ESI) mass calcd. C8H10FNO, 155.1. m/z found, 156.1 [M+H]+.
Workup
- washThe crude mixture was then washed with DCM
- extractionThe aqueous layer was extracted with DCM
- dry with materialthe combined organic extracts were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by chromatography on silica gel (0-5% MeOH in DCM)
Sources & evidence
- ORD record
- ord-d917b514dcce49609b61846058e405fb
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09066946B2
Reaction notes
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