Sodium Carbonate → HCID 83395090, compound

5-Bromothiophene-2-carbaldehyde (86.6 mg, 0.453 mmol) was added to a 20-ml microwave vial along with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (185.6 mg, 0.892 mmol), sodium carbonate (0.42 ml, 0.840 mmol, 2M), PdCl2(dppf) (68.3 mg, 0.093 mmol), dioxane (7.00 ml) and Water (2 ml). The vial was sealed and micro waved at 100° C. for 10 minutes. The reaction mixture was filtered, diluted with EtOAc and water. The organic phase was washed with brine, dried and concentrated to afford crude product, which was purified on silica gel (EtOAc/hexane-8/2) to afford 5-(1H-pyrazol-4-yl)thiophene-2-carbaldehyde (66.8 mg, 0.347 mmol, 77% yield) as a yellow-green solid. This aldehyde (66.8 mg, 0.347 mmol) and anhydrous potassium carbonate (197 mg, 1.425 mmol) were placed in a 25-ml flask and placed on high vacuum for 10 min. Under N2, anhydrous MeOH (2 ml) was added. To the suspension was added dimethyl (1-diazo-2-oxopropyl) phosphonate (0.065 ml, 0.417 mmol). The reaction was stirred at rt for 4 h. The mixture was diluted with DCM, washed with water, dried over sodium sulfate, concentrated to afford crude product (74.3 mg, 0.395 mmol, 114% yield), which was used in next step directly.

1. customThe vial was sealed
2. filtrationThe reaction mixture was filtered
3. additiondiluted with EtOAc and water
4. washThe organic phase was washed with brine
5. customdried
6. concentrationconcentrated
7. customto afford crude product, which
8. customwas purified on silica gel (EtOAc/hexane-8/2)

ORD record

ord-a7b59616312b4b71b5a90c8e7f7bbb33

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575150B2