Sodium Carbonate → 5-(3-Methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-pyridine-3-carbaldehyde

HRID 1253920Notes

Reaction equation

HRID 1253920 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[C:23]([CH:27]=[O:28])[CH:24]=[N:25][CH:26]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>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>[CH3:11][N:7]1[C:6]2[CH:12]=[C:2]([C:21]3[CH:22]=[C:23]([CH:27]=[O:28])[CH:24]=[N:25][CH:26]=3)[CH:3]=[CH:4][C:5]=2[O:9][C:8]1=[O:10]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 3374695-bromo-3-methyl-3H-benzooxazol-2-oneHCID 49926405-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbaldehyde

Product 1

HCID 866633595-(3-Methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-pyridine-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-Bromo-3-methyl-3H-benzooxazol-2-one (684 mg, 3 mmol), 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-3-carbaldehyde (699.2 mg, 3 mmol), polymer supported PalladiumTetrakis (0.11 mmol/g, 682 mg, 0.075 mmol), Na2CO3 (2 M in eater, 3 mL, 6 mmol) in DME (6 mL) was heated to reflux for overnight. After filteration and concentration, the residue was purified by flash column and yielded yellow solid. ESI-MS m/z: 255.0 [M+1]+, Retention time 1.03 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for overnight
  3. concentrationAfter filteration and concentration
  4. customthe residue was purified by flash column
  5. customyielded yellow solid

Sources & evidence

ORD record
ord-2817124651e545e183632814ed770f15
Source dataset
uspto-grants-2013_06
Patent number
US08455522B2

Reaction notes

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