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

HRID 41205

反応式

HRID 41205 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-32f03b81af134052b5cfff6e0b04df28
出典データセット
uspto-grants-2013_09
特許番号
US08530470B2

関連ノート

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