Water → HCID 60209930, 화합물

HRID 1497338노트

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HRID 1497338 반응식
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[C:7]2B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]([O:39][CH3:40])[CH:34]=1.O>C1COCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[C:7]2[CH2:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]([O:39][CH3:40])[CH:34]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 179484394-(Chloromethyl)-2-methoxypyridineHCID 60209927HCID 60209927, 화합물

생성물 1

HCID 60209930HCID 60209930, 화합물

시약·촉매·용매 3

HCID 178418807HCID 178418807, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To a mixture of methyl 8-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline-2-carboxylate (S1) (130 mg, 0.393 mmol), Cs2CO3 (384 mg, 1.178 mmol), PdCl2(dppf)-CH2Cl2 adduct (32.1 mg, 0.039 mmol) in a microwave tube were added a solution of 4-(chloromethyl)-2-methoxypyridine (124 mg, 0.785 mmol) in THF (3 mL) followed by adding water (0.3 mL). The mixture was heated at 100° C. for 1 h. The reaction was cooled and diluted with EtOAc. The bottom H2O layer was removed. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by reverse-phase HPLC (C-18 column, gradient 5-90% MeCN in H2O with both containing 0.05% TFA) to give methyl 8-fluoro-4-[(2-methoxypyridin-4-yl)methyl]quinoline-2-carboxylate (V4). ES-MS [M+1]+: 327.2.

후처리

  1. temperatureThe reaction was cooled
  2. customThe bottom H2O layer was removed
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by reverse-phase HPLC (C-18 column, gradient 5-90% MeCN in H2O with both containing 0.05% TFA)

출처 및 근거

ORD 기록
ord-02a5903297c2408e8e69cd5d00a58633
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199939B2

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