Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: Cl.[CH3:2][CH:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]([CH:17]=[O:18])=[CH:15][NH:14][N:13]=2)=[CH:8][CH:7]=1)[CH3:4].C([O-])([O-])=O.[K+].[K+].Br[CH:26]1[CH2:29][CH2:28][CH2:27]1.O>C(#N)C.CCOC(C)=O>[CH:26]1([N:14]2[CH:15]=[C:16]([CH:17]=[O:18])[C:12]([C:9]3[CH:10]=[CH:11][C:6]([O:5][CH:3]([CH3:2])[CH3:4])=[CH:7][CH:8]=3)=[N:13]2)[CH2:29][CH2:28][CH2:27]1
Reactant: CC(C)Oc1ccc(-c2n[nH]cc2C=O)cc1
Reactant: BrC1CCC1
Agent: Cl
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: CCOC(C)=O
Solvent: CC#N
Solvent: O
Product: CC(C)Oc1ccc(-c2nn(C3CCC3)cc2C=O)cc1
Temperature: 2.5 °C
Reaction time: 1 h
Yield: 85.2 %

Procedure:
A mixture of 3-[4-(propan-2-yloxy)phenyl]-1H-pyrazole-4-carbaldehyde hydrochloride (250 mg, 0.9 mmol) and K2CO3 (626 mg, 4.5 mmol) in acetonitrile (5 ml) was stirred at 0-5° C. for 1 h. Bromocyclobutane (158 mg, 1.16 mmol) was added and the reaction mixture stirred at ambient temperature for 34 h. The reaction was poured into water (200 mL) and extracted with EtOAc (50 mL×3). The combined extracts was washed with brine (100 mL), dried, and concentrated under vacuum. The residue was purified by SGC using Hexane: EtOAc (0%-40%) as eluent to afford 1-cyclobutyl-3-(4-isopropoxyphenyl)-1H-pyrazole-4-carbaldehyde (218 mg, Yield: 71%) as a white solid. LCMS (method C): RT=2.54 min, m/z=285.2 [M+H]+.
Reaction SMILES: S(Cl)(Cl)=O.[NH:5]1[CH:9]=[N:8][CH:7]=[N:6]1.[C:10]1([CH2:22][CH2:23]C=O)[C:11]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:13]=[CH:14][CH:15]=1.O.[CH2:27](Cl)[Cl:28]>>[Cl:28][CH:27]([N:5]1[CH:9]=[N:8][CH:7]=[N:6]1)[CH:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:12][C:13]1[CH:14]=[CH:15][CH:10]=[CH:22][CH:23]=1
Reactant: c1nc[nH]n1
Reactant: ClCCl
Reactant: O=CCCc1ccccc1-c1ccccc1
Solvent: O
Solvent: O=S(Cl)Cl
Product: ClC(C(Cc1ccccc1)c1ccccc1)n1cncn1
Temperature: 20 °C
Reaction time: 0.5 h
Yield: 92 %

Procedure:
At 0° C., 13.1 g of thionyl chloride is added to a solution of 15.222 g of 1,2,4-triazole in 150 ml of methylene choride. After all has been added, the mixture is stirred for 30 minutes at room temperature (20° C.): subsequently, 15.5 g of 2,3-biphenylpropanal is added. After the mixture has been stirred at room temperature for 12 to 15 hours, 100 ml of water is added and the organic phase separated off. The aqueous phase which remains is extracted by shaking twice with methylene chloride, and the collected organic phases are washed twice with saturated sodium bicarbonate solution. The isolated organic phase -s then dried over sodium sulfate and concentrated. There is obtained 30.0 g (92%) of 1-chloro-1-(1,2,4-triazol-1-yl-)2,3-diphenylpropane. The compounds listed in the table below may be obtained analogously to Example 1: