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

HRID 2243594

반응식

HRID 2243594 반응식
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

참가 물질

8

반응물 5

HCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 51483222,8,9-Triisopropyl-2,5,8,9-tetraaza-1-phosphabicyclo[3,3,3]undecaneHCID 58608099(2-[4-(4-Chloro-5-fluoro-3-phenyl-furo[2,3-b]pyridin-2-yl)-phenoxy]ethyl)dimehtylamineHCID 66683780(S)-(tetrahydrofuran-2-yl)-methylamine

생성물 1

HCID 11569111(S)-{2-[4-(2-Dimethylaminoethoxy)-phenyl]-5-fluoro-3-phenyl-furo[2,3-b]pyridin-4-yl}-[tetrahydrofuran-2-ylmethyl]-amine

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  1. customwas degassed three times
  2. customThe solvent was removed
  3. customthe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-02c9e2815a0647cd8df6a3aaa586eefb
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674907B2

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