Preheat your oven to 350°F (175°C) and grease your pan with butter, then line it with parchment paper.

In a saucepan over medium heat, melt 1/4 cup of unsalted butter until bubbly, then mix in 1/2 cup of granulated sugar.

Add 2 cups of cherries and 1 teaspoon of vanilla extract, stirring until combined. Pour this cherry mixture into the prepared pan.

In a large mixing bowl, sift together 1 1/2 cups of all-purpose flour, 1 cup of granulated sugar, 3/4 cup of cocoa powder, 1 teaspoon of baking powder, 1/2 teaspoon of baking soda, and 1/2 teaspoon of salt.

In another bowl, whisk 2 large eggs, 1 cup of buttermilk, 1/2 cup of vegetable oil, and 1 teaspoon of vanilla extract. Gradually add the wet ingredients to the dry mix, then stir in 1 cup of boiling water until smooth.

Carefully pour the chocolate cake batter over the cherry mixture in the pan, ensuring it spreads evenly.

Place the pan in the preheated oven and bake for 35-40 minutes. To check, insert a toothpick; it should come out clean.

Once baked, let the cake cool in the pan for about 10 minutes. Run a knife around the edges to loosen the cake and invert it onto a serving platter.

Allow it to cool for additional minutes before serving.