Reaction SMILES: [C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([CH2:16]OS(C)(=O)=O)[S:15][C:11]=2[C:10]([I:22])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>ClCCl>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([CH2:16][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[S:15][C:11]=2[C:10]([I:22])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
Reactant: C1CCNCC1
Reactant: CC(C)(C)OC(=O)n1nc(I)c2sc(COS(C)(=O)=O)cc21
Solvent: CCN(CC)CC
Solvent: ClCCl
Product: CC(C)(C)OC(=O)n1nc(I)c2sc(CN3CCCCC3)cc21
Temperature: 25 °C
Reaction time: 1 h
Yield: 53.5 %

Procedure:
To 5-(tert-butyl-dimethyl-silanyloxymethyl)-3-iodo-thieno[3,2-c]pyrazole-l1-carboxylic acid tert-butyl ester [410 mg, 0.83 mmol, Intermediate (73)] in tetrahydrofuran (5 mL) was added a 1.0M TBAF solution in tetrahydrofuran (0.92 mL, 0.92 mmol) at 0° C. The solution was stirred at 0° C. for 1 hour. The solvent was removed and the residue was chromatographed through silica gel (dichloromethane/ethyl acetate, 90/10as eluant) to afford 5-hydroxymethyl-3-iodo-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [230 mg, 73%, Intermediate (80)] as a white powder. LC/MS: 380.97 (M+H), RT=2.8 minutes. Step 2. To 5-hydroxymethyl-3-iodo-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [220 mg, 0.58 mmol, Intermediate (80)] in dichloromethane (5 mL) were added triethylamine (85 μL, 0.67 mmol), and methane sulfonyl chloride (50 μL, 0.67 mmol). The mixture was stirred at 0° C. for 15 minutes then at room temperature for 30 minutes. The solution was washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate and concentrated to afford 3-iodo-5-methanesulfonyloxymethyl-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [220 mg, 79%, Intermediate (81)] as a white foam. LC/MS: 458.97 (M+H), RT=3.39 minutes. Step 3. To 3-iodo-5-methanesulfonyloxymethyl-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [210 mg, 0.46 mmol, Intermediate (81)] in dichloromethane (3 mL) were added triethylamine (70 μL, 0.55 mmol), and piperidine (55 μL, 0.55 mmol). The mixture was stirred at room temperature for 1 hour. The solvent was removed and the residue was chromatographed through silica gel (dichloromethane/ethyl acetate, 95/05 as eluant) to produce 3-iodo-5-piperidin-1-ylmethyl-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [110 mg, 53%, Intermediate (82)] as a white foam. LC/MS: 448.0 (M+H), RT=2.55 minutes. Step 4. To 3-iodo-5-piperidin-1-ylmethyl-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [390 mg, 0.87 mmol, Intermediate (82)] in 1,4-dioxane (8 mL) were added 5-(tert-butyl-dimethyl-silanyloxymethyl)-1H-indole-2-boronic acid 1-carboxylic acid tert-butyl ester (450 mg, 1.13 mmol, Intermediate (8), prepared as described in Example 1-4 of International Patent Application Publication No. WO 02/32861], and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (complex with dichloromethane (1:1)) (50 mg, 0.07 mmol), followed by cesium carbonate (1.13 g, 3.48 mmol) and water (3 mL). The mixture was stirred at 80° C. for 3 hours. It was then extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The residual oil was chromatographed through silica gel (dichloromethane/methanol, 95/05 as eluant) to produce 2-(1-tert-butoxycarbonyl-5-piperidin-1-ylmethyl-1H-thieno [3,2-c]pyrazol-3-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-indole-1-carboxylic acid tert-butyl ester [310 mg, 53%, Intermediate (83)] as a white powder. LC/MS: 681.33 (M+H), RT=3.88 minutes. Step 5. To 2-(1-tert-butoxycarbonyl-5-piperidin-1-ylmethyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-indole-1-carboxylic acid tert-butyl ester [530 mg, 0.78 mmol, Intermediate (83)] in tetrahydrofuran (10 mL) at 0° C. was added a 1M solution of TBAF in tetrahydrofuran (0.86, 0.86 mmol). The mixture was stirred at 0° C. for 2 hours. It was diluted with ethyl acetate and washed with saturated aqueous ammonium chloride. The organic layer was dried over magnesium sulfate and concentrated. The residue was chromatographed through silica gel (n-heptane/ethyl acetate, 80/20 as eluant) to afford 2-(1-tert-butoxycarbonyl-5-piperidin-1-ylmethyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester [305 mg, 70%, Intermediate (84)] as a white foam. LC/MS: 567.3 (M+H), RT=2.89 minutes. Step 6. To 2-(1-tert-butoxycarbonyl-5-piperidin-1-ylmethyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester [280 mg, 0.50 mmol, Intermediate (84)] in a mixture of tetrahydrofuran (5 mL) and water (1 mL) was added sodium hydroxide (150 mg, 3.75 mmol). The mixture was stirred at 65° C. overnight. It was diluted with ethyl acetate. The mixture was washed with saturated aqueous ammonium chloride. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated. The residue was chromatographed through silica gel (dichloromethane/1.0M ammonia in methanol, 95/05 then 50/50 as eluant) to produce [2-(5-piperidin-1-ylmethyl-1H-thieno[3,2-c]pyrazol-3-yl)-1H-indol-5-yl]-methanol [10 mg, 5%, Example 68] as a white powder. LC/MS: 367.1 (M+H), RT=2.22 minutes; 1H NMR [300 Mhz, (CD3)2SO]: δ 13.08 (s, 1H), 11.45 (s, 1H), 7.47 (s, 1H), 7.34 (d, J=8.2 Hz, 1H), 7.07 (s, 1H), 7.05 (s, 1H), 6.57 (s, 1H), 4.98 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.71 (s, 2H), 2.44 (m, 4H), 1.53 (m, 4H), 1.42 (m, 2H).