Hello Ryfus,
Welcome to Apple Support Communities. Are you running any anti-virus software on that iPad? If so, try disabling it, and test the issue. You can also try enabling Wi-Fi sync to Finder. The steps are found in the Apple Support article: Use the Finder to sync your iPhone, iPad, or iPod with your computer - Apple Support
Sync your content using Wi-Fi
After you set up syncing with the Finder using USB, you can set up the Finder to sync to your device with Wi-Fi instead of USB.
- Connect your device to your computer with a USB cable, then open a Finder window and select your device.
- Select “Show this [device] when on Wi-Fi."
- Click Apply.
When the computer and the device are on the same Wi-Fi network, the device appears in the Finder. The device syncs automatically whenever it's plugged in to power.
Let us know if you have any questions.
Best regards!