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ノート

反応式

HRID 2243594 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-02c9e2815a0647cd8df6a3aaa586eefb
出典データセット
uspto-grants-2010_03
特許番号
US07674907B2

反応ノート

読み込み中…