In the bowl of a stand mixer combine flour, sugar and yeast and mix. Slowly while mixing add milk, butter, egg, vanilla and salt. Knead for 5 minutes or until smooth.
Place in a greased bowl and cover with a towel for 3 hours. Then 30 minutes in the fridge. When it’s chilled, the dough is easier to work with. Or you can skip the first 3 hours and leave it in the fridge overnight.
Preheat oven to 375℉/190℃.
Prepare the filling. In a microwave safe bowl melt butter. Add maple syrup, brown sugar, and cinnamon, stir well. Add chocolate and microwave for 30 seconds or until melted.
Grease a loaf pan.
Roll out the dough into a big square. Cover it with the chocolate mixture and sprinkle with pecans. Roll it up! Cut the roll in half both crosswise and lengthwise so you have 4 even strands with cut parts facing up.
Braid the 4 strands as you like (refer to video). Place in a prepared loaf pan and bake for 30 minutes.
Microwave sugar and water until dissolved and pour over babka when it comes out of the oven and still hot. Let cool and serve.