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

HRID 41205
Notes
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Reaction equation

HRID 41205 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-32f03b81af134052b5cfff6e0b04df28
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08530470B2

Reaction notes

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