Piperidine → HCID 66599464, 화합물

HRID 2410854노트

반응식

HRID 2410854 반응식
[CH2:1]([N:8]1[C:16]2[CH:15]=[C:14]([O:17][CH3:18])[CH:13]=[CH:12][C:11]=2[C:10]2[N:19]=[C:20](Br)[CH:21]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[NH:76]1[CH2:81][CH2:80][CH2:79][CH2:78][CH2:77]1>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].O1CCOCC1>[CH2:1]([N:8]1[C:16]2[CH:15]=[C:14]([O:17][CH3:18])[CH:13]=[CH:12][C:11]=2[C:10]2[N:19]=[C:20]([N:76]3[CH2:81][CH2:80][CH2:79][CH2:78][CH2:77]3)[CH:21]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 8082PiperidineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86663064HCID 86663064, 화합물

생성물 1

HCID 66599464HCID 66599464, 화합물수율 57.1%

시약·촉매·용매 3

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A vial containing a mixture of methyl 5-benzyl-2-bromo-7-methoxy-5H-pyrido[3,2-b]indole-4-carboxylate (90 mg, 0.21 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (18 mg, 0.032 mmol), tris(dibenzylideneacetone)dipalladium-chloroform adduct (11 mg, 11 μmol), Cs2CO3 (56 mg, 0.53 mmol) was flushed with nitrogen. Dioxane (1 mL) and piperidine (0.042 mL, 0.42 mmol) was added and the vial was sealed and heated at 100° C. overnight. This was then diluted with EtOAc, washed with water and brine, and dried over Na2SO4. Removal of the solvent followed by radial silica gel chromatography (step gradient elution with DCM containing 0 to 2% MeOH) afforded methyl 5-benzyl-7-methoxy-2-(piperidin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (51 mg, 0.12 mmol, 56% yield) as a solid. MS (ESI) m/z 430.2 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 8.15 (1H, d, J=8.55 Hz), 7.25 (1H, s), 7.15-7.21 (2H, m), 6.89-6.94 (3H, m), 6.87 (1H, dd, J=8.55, 2.14 Hz), 6.78 (1H, d, J=2.14 Hz), 5.59 (2H, s), 3.84 (3H, s), 3.66 (3H, s), 3.53-3.61 (4H, m), 1.68-1.76 (4H, m), 1.61-1.68 (2H, m).

후처리

  1. additionA vial containing
  2. customwas flushed with nitrogen
  3. customthe vial was sealed
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent
  7. washfollowed by radial silica gel chromatography (step gradient elution with DCM containing 0 to 2% MeOH)

출처 및 근거

ORD 기록
ord-84ba0ce988d445808cd58e3a796afc08
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815840B2

반응 노트

불러오는 중…