Cesium carbonate → 8-(1-(3-fluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

HRID 41205

반응식

HRID 41205 반응식
[CH3:1][N:2]([CH3:27])[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([CH:15]3[CH2:19][CH2:18][CH2:17][NH:16]3)[CH:14]=1)[O:11][C:10]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[CH:9][C:8]2=[O:26])=[O:4].Br[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=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+]>O1CCOCC1.C(O[Pd]OC(=O)C)(=O)C>[F:35][C:31]1[CH:30]=[C:29]([N:16]2[CH2:17][CH2:18][CH2:19][CH:15]2[C:13]2[CH:14]=[C:5]([C:3]([N:2]([CH3:27])[CH3:1])=[O:4])[CH:6]=[C:7]3[C:12]=2[O:11][C:10]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:9][C:8]3=[O:26])[CH:34]=[CH:33][CH:32]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 140821-Bromo-3-fluorobenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86672428N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide

생성물 1

HCID 665579688-(1-(3-fluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide수율 41.1%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

Diacetoxypalladium (3.9 mg, 0.02 mmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (130 mg, 0.35 mmol), 1-bromo-3-fluorobenzene (0.049 ml, 0.44 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (20.25 mg, 0.03 mmol) and cesium carbonate (171 mg, 0.52 mmol) dissolved in 1,4-dioxane (4 mL). The resulting suspension was degassed with argon and stirred at 100° C. for 16 h then cooled to room temperature, filtered and concentrated. The crude product was dissolved in DMA (2 mL) and purified by preparative HPLC. The fractions containing the desired compound were evaporated to dryness to afford 8-(1-(3-fluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (67 mg, 41%) as a solid.

후처리

  1. customThe resulting suspension was degassed with argon
  2. temperaturethen cooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe crude product was dissolved in DMA (2 mL)
  6. custompurified by preparative HPLC
  7. additionThe fractions containing the desired compound
  8. customwere evaporated to dryness

출처 및 근거

ORD 기록
ord-32f03b81af134052b5cfff6e0b04df28
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530470B2

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