"He likes singing in the rain."
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下雨 = to rain (a verb)
雨 = rain (noun-thing)
雨里 = in the rain (noun-place)
When you want to say something is happening or located at a certain place you use 在 (to be located at).
他在家 = He is at home
他在家睡觉 = He is at home sleeping / He is sleeping at home
他喜欢 + 在家 + 睡觉
He likes + to be located at home + to sleep / He likes sleeping at home
Your sentence is missing the location aspect. You have a subject followed by 3 verbs. He + likes + to rain + to sing. You need to say where he likes to sing by using "在 + place".