Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [OH-].[NH4+:2].[C:3]([C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH3:19])(OCC)=[O:4]>C(O)C>[C:3]([C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH3:19])(=[O:4])[NH2:2]
Reactant: [NH4+]
Reactant: CCOC(=O)c1oc(-c2ccccc2)nc1C
Agent: [OH-]
Solvent: CCO
Product: Cc1nc(-c2ccccc2)oc1C(N)=O
Temperature: 25 °C
Reaction time: 72 h

Procedure:
150 Ml. (2.5 mole) of concentrated ammonium hydroxide is added dropwise to a solution of 10 g. (0.0434 mole) of 5-carbethoxy-2-phenyl-4-methyloxazole in 150 ml. of 95% ethanol. The mixture is stirred three days at room temperature, then it is concentrated to 50 ml. by evaporating the ethanol and chilled. The precipitated product is filtered, washed, dried over sodium sulfate and recrystallized from methanol; yield 3.7 g. of the title compound; m.p. 187°-190°.
Reaction SMILES: [Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[CH3:20])[CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.Cl.[CH3:22][NH:23][O:24][CH3:25]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[CH3:20])[CH2:9][C:10]([N:23]([O:24][CH3:25])[CH3:22])=[O:11])=[CH:4][CH:3]=1
Reactant: Cc1cc(F)ccc1C(CC(=O)O)c1ccc(Br)cc1
Reactant: CNOC
Agent: Cl
Product: CON(C)C(=O)CC(c1ccc(Br)cc1)c1ccc(F)cc1C

Procedure:
In analogy to example 74, step 4, from 3-(4-bromophenyl)-3-(4-fluoro-2-methylphenyl)-propanoic acid and N,O-dimethylhydroxylamine hydrochloride was prepared the title compound as a colorless oil, MS (ESI+): m/z=382.06 [M+H]+.
Reaction SMILES: [Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:25])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CCCCCC.CCOC(C)=O>[Br:25][C:8]1[NH:9][C:10]2[C:15]([C:7]=1[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:17][CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2
Reactant: Clc1ccc(Cc2c[nH]c3ccccc23)cc1
Reactant: O=C1CCC(=O)N1Br
Solvent: CCOC(C)=O
Solvent: ClC(Cl)(Cl)Cl
Solvent: CCCCCC
Product: Clc1ccc(Cc2c(Br)[nH]c3ccccc23)cc1
Temperature: 25 °C
Reaction time: 1 h

Procedure:
To a solution of 2 g of 3-(4-chlorobenzyl)-1H-indole in 50 mL of CCl4 was added 1.8 g of NBS. The reaction mixture was stirred for 1 hour at room temperature and diluted with 50 mL of 5:1 hexane/EtOAc. The mixture was then filtered through a pad of silica gel and the filtrate was concentrated under reduced pressure to give the crude title compound, which was used for the next step without further purification.
Reaction SMILES: [Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:18])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.Br[C:20]1C=CC(C(C)(C)CO)=CC=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:20])([CH3:18])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])=[CH:6][CH:7]=1
Reactant: CC(CO[Si](C)(C)C(C)(C)C)c1ccc(Br)cc1
Reactant: CC(C)(CO)c1ccc(Br)cc1
Product: CC(C)(CO[Si](C)(C)C(C)(C)C)c1ccc(Br)cc1

Procedure:
According to the procedure for the preparation of 73C, 74A (1.93 g, 8.42 mmol) afforded 3.04 g of 74B as a colorless oil. MS (ESI) m/z 211.1 (M-OTBS)+.