Water → HCID 18452165, compound

HRID 1271205Notes

Reaction equation

HRID 1271205 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([CH:16]=[O:17])[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][C:7]1=[O:18].[N:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C.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>[O:18]=[C:7]1[N:6]([CH2:5][C:4]2[CH:19]=[CH:20][CH:21]=[C:2]([C:25]3[CH:26]=[CH:27][N:22]=[CH:23][CH:24]=3)[CH:3]=2)[C:11]2[CH:12]=[C:13]([CH:16]=[O:17])[CH:14]=[CH:15][C:10]=2[O:9][CH2:8]1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 18452271HCID 18452271, compound

Product 1

HCID 18452165HCID 18452165, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(3-iodo-benzyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde (0.100 g, 0.254 mmol) and Pd(PPh3)4 (0.015 g, 0.01 mmol) in DMF (20.0 mL) was added pyridine-4-boronic acid (0.034 g, 0.279 mmol) followed by the addition of Na2CO3 (2 mL, 2.0 M solution). The solution was heated to reflux overnight with good stirring. The heat was turned off, the solution was poured into H2O (30 mL), and the organic phase was extracted with CH2Cl2 (3×40 mL). The organic phase was than dried over MgSO4, filtered, and concentrated down under reduced pressure. The product was chromatographed with CH2Cl2/MeOH (9:1).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux overnight with good stirring
  3. extractionthe organic phase was extracted with CH2Cl2 (3×40 mL)
  4. dry with materialthan dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated down under reduced pressure
  7. customThe product was chromatographed with CH2Cl2/MeOH (9:1)

Sources & evidence

ORD record
ord-ec24cb69ef994bf2b64bad523e109f23
Source dataset
uspto-grants-2007_04
Patent number
US07205295B2

Reaction notes

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