Potassium Carbonate → (S)-{2-[4-(2-Dimethylaminoethoxy)-phenyl]-5-fluoro-3-phenyl-furo[2,3-b]pyridin-4-yl}-[tetrahydrofuran-2-ylmethyl]-amine

HRID 2243594Notes

Reaction equation

Cl[C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[O:9][C:10]([C:18]3[CH:29]=[CH:28][C:21]([O:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=3)=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:3]=12.[O:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1NC.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([O-])([O-])=O.[K+].[K+].[CH:89]([N:92]1CCN2CCN(C(C)C)P1N(C(C)C)CC2)(C)C>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:26][N:25]([CH3:27])[CH2:24][CH2:23][O:22][C:21]1[CH:28]=[CH:29][C:18]([C:10]2[O:9][C:4]3=[N:5][CH:6]=[C:7]([F:8])[C:2]([NH:92][CH2:89][C@@H:31]4[CH2:32][CH2:33][CH2:34][O:30]4)=[C:3]3[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The mixture of (2-[4-(4-chloro-5-fluoro-3-phenyl-furo[2,3-b]pyridin-2-yl)-phenoxy]-ethyl)-dimehtylamine (7) (10.0 mg, 0.024 mmol), (S)-(tetrahydrofuran-2-yl)-methylamine (5.0 mg, 0.048 mmol), Pd(OAc)2 (1.0 mg, 0.003 mmol), BINAP (2.0 mg, 0.003 mmol), K2CO3 (3.3 mg, 0.024 mmol) and Vercada Base, 2,8,9-triisopropyl-2,5,8,9-tetraaza-1-phosphabicyclo[3,3,3]undecane (cat) in toluene (0.8 mL) was degassed three times and heated to 100° C. with stirring under N2 for 3.5 h. The solvent was removed and the residue was purified by preparative HPLC to give the title compound.

Workup

customwas degassed three times
customThe solvent was removed
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-02c9e2815a0647cd8df6a3aaa586eefb
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674907B2

Reaction notes

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