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1-Bromo-4-fluorobenzene → 8-(1-(4-fluorophenyl)pyrrolidin-2-yl)-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-one

HRID 41200
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HRID 41200 반응식
[N:1]1([C:7]([C:9]2[CH:10]=[C:11]3[C:16](=[C:17]([CH:19]4[CH2:23][CH2:22][CH2:21][NH:20]4)[CH:18]=2)[O:15][C:14]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:13][C:12]3=[O:30])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.Br[C:57]1[CH:62]=[CH:61][C:60]([F:63])=[CH:59][CH:58]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(O[Pd]OC(=O)C)(=O)C>[F:63][C:60]1[CH:61]=[CH:62][C:57]([N:20]2[CH2:21][CH2:22][CH2:23][CH:19]2[C:17]2[CH:18]=[C:9]([C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[O:8])[CH:10]=[C:11]3[C:16]=2[O:15][C:14]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)=[CH:13][C:12]3=[O:30])=[CH:58][CH:59]=1
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참가 물질

7

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HCID 99931-Bromo-4-fluorobenzeneHCID 10796Cesium carbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 866724156-(morpholine-4-carbonyl)-2-morpholino-8-(pyrrolidin-2-yl)-4H-chromen-4-one

생성물 1

HCID 866724248-(1-(4-fluorophenyl)pyrrolidin-2-yl)-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-one수율 46%

시약·촉매·용매 2

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

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온도
100 °C

실험 절차

Diacetoxypalladium (6.79 mg, 0.03 mmol) was added to a stirred mixture of 6-(morpholine-4-carbonyl)-2-morpholino-8-(pyrrolidin-2-yl)-4H-chromen-4-one (250 mg, 0.60 mmol), biphenyl-2-yldicyclohexylphosphine (21 mg, 0.06 mmol), 1-bromo-4-fluorobenzene (0.083 ml, 0.76 mmol) and cesium carbonate (296 mg, 0.91 mmol) dissolved in 1,4-dioxane (5 mL). The resulting suspension was degassed with argon and then stirred at 100° C. for 15 h. The reaction mixture was purified by preparative HPLC. The fractions containing the desired compound were evaporated to dryness to afford 8-(1-(4-fluorophenyl)pyrrolidin-2-yl)-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-one (140 mg, 46%) as a gum.

후처리

  1. customThe resulting suspension was degassed with argon
  2. customThe reaction mixture was purified by preparative HPLC
  3. additionThe fractions containing the desired compound
  4. customwere evaporated to dryness

출처 및 근거

ORD 기록
ord-8a99fb9e15b94638bc13434adb44e97e
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08530470B2

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