truncate table Reports 
go

IF OBJECT_ID('tempdb..#temp') IS NOT NULL
    DROP TABLE #temp

CREATE TABLE #temp(
[files] [nvarchar](50) NULL
--[Warrants] [nvarchar](50) NULL,
--	[Statement] [nvarchar](50) NULL,
--	[Property Tax] [nvarchar](50) NULL
) ON [PRIMARY]
go

INSERT INTO #temp
EXEC xp_cmdshell 'dir D:\Reports /b'

;WITH cte AS
(
	SELECT
		CASE 
			WHEN files LIKE '%stmt.pdf' THEN 'stmt'
			WHEN files LIKE '%tax.pdf' THEN 'tax'
			WHEN files LIKE '%warr.xls' THEN 'warr'
		END
		AS FileType,
		REPLACE(REPLACE(REPLACE(files,'stmt.pdf',''),'tax.pdf',''),'warr.xls','') AS FILENAME,
		files
	FROM
		#temp
)
INSERT INTO Reports
([Statement],[Property Tax],[Warrants], [FileName])
SELECT
	stmt, tax, warr, FileName
FROM
	cte
PIVOT(MAX(files) FOR filetype IN ([stmt],[tax],[warr]))p