2-bromo-5-(1,3-oxazol-2-yl)benzaldehyde → HCID 15895425, compound

HRID 1637707Notes

Reaction equation

HRID 1637707 reaction equation
B([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([C:20]1[C:24]([CH3:25])=[C:23]([CH3:26])[O:22][N:21]=1)[CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])(=[O:12])=[O:11])(O)O.Br[C:28]1[CH:35]=[CH:34][C:33]([C:36]2[O:37][CH:38]=[CH:39][N:40]=2)=[CH:32][C:29]=1[CH:30]=[O:31]>C1(C)C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].CCOC(C)=O.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>[CH3:25][C:24]1[C:20]([N:13]([CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[S:10]([C:5]2[C:4]([C:28]3[CH:35]=[CH:34][C:33]([C:36]4[O:37][CH:38]=[CH:39][N:40]=4)=[CH:32][C:29]=3[CH:30]=[O:31])=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:12])=[O:11])=[N:21][O:22][C:23]=1[CH3:26]

Participants

8

Reactant 2

HCID 107059332-bromo-5-(1,3-oxazol-2-yl)benzaldehydeHCID 11728709HCID 11728709, compound

Product 1

HCID 15895425HCID 15895425, compound

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
85 °C

Procedure

To the 2-borono-N-(4,5-dimethyl-3-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide and 2-bromo-5-(2-oxazolyl)benzaldehyde (13.32 g, 58.14 mmol, prepared as described in Example 21 of European Patent Application No. 702,012) in 264 ml of toluene and 132 ml of 95% ethanol ("EtOH"), 106 ml 2M aqueous sodium carbonate and tetrakis(triphenylphosphine)palladium(0) (6.11 g, 5.29 mmol) were added and the reaction mixture heated under argon at 85° C. for 4 hrs, cooled and diluted with 250 ml of EtOAc. The organic layer was separated and washed with 100 ml H2O and 50 ml brine, dried and concentrated. The residue was chromatographed on silica gel using 1:1 hexane/EtOAc to afford the title product of this step (16.95 g, 62.7% for two steps) as a colorless gum.

Workup

  1. temperaturecooled
  2. customThe organic layer was separated
  3. washwashed with 100 ml H2O and 50 ml brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel using 1:1 hexane/EtOAc

Sources & evidence

ORD record
ord-4667c5e162a44d8eaa4b3b625088fc19
Source dataset
uspto-grants-2000_03
Patent number
US06043265

Reaction notes

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