  The latest LHC collaborations results on $\sigma_{H^{\pm}}BR(H^{\pm}
\rightarrow \tau^{\pm}\nu)$ and $\sigma_{H^{\pm}}BR(H^{+} \rightarrow
t\bar{b})$ are used to impose constraints on the charged Higgs $H^{\pm}$
parameters within the Two Higgs Doublet Model (2HDM). But it leaves $1.5 \leq
tan \beta \leq 3$ window unexplored where the $BR(H^{\pm} \rightarrow
W^{\pm}h)$ becomes sizable for $m_{H^{\pm}} > m_{t}$. In this manuscript
$H^{\pm} \rightarrow W^{\pm}h$ is investigated with neutral Higgs boson
decaying to a pair of b-quarks and the discovery prospects of charged Higgs
boson is discussed. In particular, the analysis is optimized by putting the
kinematic cuts and prospects of using Machine Learning Technique to derive
values of $\sigma\times BR$ needed for a $5 \sigma$ discovery at the LHC.
