Water → HCID 59026084, compound

HRID 639019Notes

Reaction equation

HRID 639019 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[O:15][CH2:14][CH2:13][O:12][C:10]3=2)[N:5]=[CH:4][C:3]=1[Cl:16].O.C([O-])([O-])=O.[K+].[K+].B1(C=C)OB([CH:30]=[CH2:31])OB(C=C)O1.C1C=CN=CC=1>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:16][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[CH:30]=[CH2:31])=[C:10]1[O:12][CH2:13][CH2:14][O:15][C:9]1=[CH:8][CH:7]=2

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 59026172HCID 59026172, compound

Product 1

HCID 59026084HCID 59026084, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 10-Bromo-9-chloro-2,3-dihydro-[1,4]dioxino[2,3-f]quinoline (11.5 g, 38.4 mmol, 1 eq) in DME (425 mL, degassed with Argon), was added Pd(PPh3)4, the reaction was stirred under Argon for 20 mins. Water (122 mL), K2CO3 (5.32 g, 38.4 mmol, 1 eq) and the 2,4,6-trivinylcyclotriboroxane-pyridine complex (2.49 g, 15.4 mmol, 0.4 eq) were added, the mixture was then heated to reflux at 100° C. overnight. The reaction was then cooled, the product was extracted with water and DCM, dried over Na2SO4, filtered and evaporated to dryness. The solid obtained was the passed through silica with as a pale yellow solid (5.5 g, 58%). LC/MS (ES) m/z 247 (MH+ 100%); 1H-NMR (400 MHz, CDCl), 8.69 (1H, s, CHNHC), 7.59 (1H, d, J=9.2, CHCO), 7.18 (1H, dd, J=18, 12, CCH═C), 5.68 (1H, dd, J=12, 1, Hcis of CH2=C), 5.49 (1H, dd, J=18, 1, H trans of CH2=C), 4.37-4.339 (4H, m, 2×(CH2O)).

Workup

  1. temperaturethe mixture was then heated
  2. temperatureThe reaction was then cooled
  3. extractionthe product was extracted with water and DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe solid obtained

Sources & evidence

ORD record
ord-beedd1a949984ee084380a000ac454d3
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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