The pattern should actually be fine up to 37*54 = (37*3)*18 = 1998; it breaks at 37*57 because that’s (37*3)*19 and 1+9 isn’t less than 10.
Similarly interesting patterns will crop up when multiplying 1111 or 11111 by integers - and similarly in other bases as well (identically, in fact - multiples of 0x111 include 0x1221, 0x1332, etc)
So this sort of reduces to ‘I guess It’s funny that 111 is 37*3’.. but on some level, that’s just how numbers work. Every number has a prime factorization. 1111’s prime factors are 11 and 101. 0x111’s prime factors are 0x3, 0x7 and 0xD; 111’s just happen to be 3 and 37.
That said… it turns out 37 crops up as a prime factor of 111, 111111, 111111111, 111111111111… so there’s something a little more going on here…
Although even that is really just because each of those numbers is 111* a number of the form 1001…001001001 - 1000^0+1000^1+…+1000^n