Using integration by parts:
$$\int_\frac{\pi}{4}^\frac{\pi}{2}\cos\left(2x\right)\ln\left(\sin\left(x\right)\right)\space\text{d}x=\left[\frac{\sin\left(2x\right)\ln\left(\sin\left(x\right)\right)}{2}\right]_\frac{\pi}{4}^\frac{\pi}{2}-\int_\frac{\pi}{4}^\frac{\pi}{2}\frac{\cos\left(x\right)\sin\left(2x\right)}{2\sin\left(x\right)}\space\text{d}x\tag1$$
Now, see that:
$$\left[\frac{\sin\left(2x\right)\ln\left(\sin\left(x\right)\right)}{2}\right]_\frac{\pi}{4}^\frac{\pi}{2}=\frac{\sin\left(2\cdot\frac{\pi}{2}\right)\ln\left(\sin\left(\frac{\pi}{2}\right)\right)}{2}-\frac{\sin\left(2\cdot\frac{\pi}{4}\right)\ln\left(\sin\left(\frac{\pi}{4}\right)\right)}{2}=\frac{\ln2}{4}\tag2$$
And for the integral, substitute $\text{u}=\tan\left(x\right)$:
$$\int_\frac{\pi}{4}^\frac{\pi}{2}\frac{\cos\left(x\right)\sin\left(2x\right)}{2\sin\left(x\right)}\space\text{d}x=\frac{1}{2}\int_1^\infty\frac{1}{\left(1+\text{u}^2\right)^2}\space\text{d}\text{u}=\frac{1}{2}\int_1^\infty\frac{1}{1+\text{u}^2}\space\text{d}\text{u}-\frac{1}{4}\tag3$$