Water → HCID 9904649, 화합물

HRID 33284

반응식

HRID 33284 반응식
Br[C:2]1[NH:3][C:4]2[CH:5]=[CH:6][CH:7]=[C:8]3[C:14](=[O:15])[NH:13][CH2:12][CH2:11][C:10]=1[C:9]=23.C([O-])([O-])=O.[K+].[K+].[N+:22]([C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)([O-:24])=[O:23].O>O1CCOCC1>[N+:22]([C:25]1[CH:30]=[C:29]([C:2]2[NH:3][C:4]3[CH:5]=[CH:6][CH:7]=[C:8]4[C:14](=[O:15])[NH:13][CH2:12][CH2:11][C:10]=2[C:9]=34)[CH:28]=[CH:27][CH:26]=1)([O-:24])=[O:23]

참가 물질

6

반응물 4

HCID 962WaterHCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 99432302-Bromo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one

생성물 1

HCID 9904649HCID 9904649, 화합물

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

Tricyclic bromide 11 (27 mg, 0.10 mmol) in 1,4-dioxane (1.0 mL) was treated with solid K2CO3 (41 mg, 0.30 mmol), m-nitrophenylboronic acid (34 mg, 0.20 mmol), and water (0.25 mL). The solution was degassed and tetrakis(triphenylphosphine)palladium(0) (12 mg, 10 mol %) was added. The solution was heated at 100° C. for 1 h, then cooled to ambient temperature and diluted with water (2 mL). The aqueous layer was adjusted to pH=7-8 with saturated aqueous K2CO3 and extracted with EtOAc (5 mL×3). The organic solution was washed with water and brine, dried (Na2SO4), filtered, and concentrated. The crude product was purified by flash chromatography (3-5% MeOH in CHCl3) to yield 14 as a yellow solid, 26.3 mg (87%). mp 268-270° C. (dec.); 1H NMR (DMSO-d6) δ 3.16 (m, 2H), 3.45 (m, 2H), 7.33 (m, 1H), 7.65 (m, 1H), 7.76 (m, 1H), 7.78 (m, 1H), 8.30 (m, 1H), 8.53 (bs, 1H), 8.16 (m, 2H), 11.93 (bs, 1H); HRMS (M+Na) Calcd for C17H13N3O3+Na: 330.0855, Found: 330.0847; Anal. (C17H13N3O3.H2O) C, H, N.

후처리

  1. customThe solution was degassed
  2. additiontetrakis(triphenylphosphine)palladium(0) (12 mg, 10 mol %) was added
  3. temperaturecooled to ambient temperature
  4. additiondiluted with water (2 mL)
  5. extractionextracted with EtOAc (5 mL×3)
  6. washThe organic solution was washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography (3-5% MeOH in CHCl3)

출처 및 근거

ORD 기록
ord-9d936bc5752f40afbcb7fc79956b40a6
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429578B2

연결된 노트

불러오는 중…