Nitrogen → HCID 11218715, compound

HRID 1640330Notes

Reaction equation

HRID 1640330 reaction equation
Br[C:2]1[O:3][C:4]2[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=2[C:6]=1[CH2:7][OH:8].[CH:13]([C:15]1[O:16][C:17](B(O)O)=[CH:18][CH:19]=1)=[O:14].C(=O)([O-])[O-].[K+].[K+].N#N>C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd].O.CC(N(C)C)=O>[CH:13]([C:15]1[O:16][C:17]([C:2]2[O:3][C:4]3[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=3[C:6]=2[CH2:7][OH:8])=[CH:18][CH:19]=1)=[O:14]

Participants

8

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 27343555-Formylfuran-2-boronic acidHCID 13225968HCID 13225968, compound

Product 1

HCID 11218715HCID 11218715, compound

Reagents, catalysts & solvents 3

HCID 72499888Dibenzalacetone palladiumCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To the bromo-benzofuran derivative from Step B (0.1 mmol), 2-formylfuran-5-boronic acid (1.5 equiv.), potassium carbonate (1.5 equiv.), palladium dibenzylidene acetone (0.03 eq.) and degassed dimethylacetamide (1 ml) was added. The mixture was blanketed with N2 and heated in a microwave reactor at 120° C. for 10 mins (initial power 50 W). Water (2 mL) was added, the mixture extracted with ether (4×10 mL), the crude extract adsorbed on silica gel, and purified by MPLC (hexanes/ethyl acetate gradient). MS (m/e): 242 (M+), 225, 213, 196, 185, 168, 157, 139, 128, 102, 77. 1H-NMR (acetone-D6): 5.15 (s, 2H), 7.19 (d, 1H, J=4 Hz), 7.35 (dd, 1H, J=8 Hz, 1 Hz), 7.44 (dd, 1H, J=8 Hz, 1 Hz), 7.56-7.65 (m, 2H), 7.93 (d, 1H, J=8 Hz), 9.76 (s, 1H). 13C-NMR (acetone-D6).

Workup

  1. additionwas added
  2. extractionthe mixture extracted with ether (4×10 mL)
  3. extractionthe crude extract
  4. custompurified by MPLC (hexanes/ethyl acetate gradient)

Sources & evidence

ORD record
ord-69a2f27cd7514a1cacf9166465894c04
Source dataset
uspto-grants-2012_02
Patent number
US08114382B2

Reaction notes

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