3-Chloro-4-fluoroaniline → HCID 9077377, compound

HRID 1845754Notes

Reaction equation

HRID 1845754 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[C:7]([OH:9])=O.CCN(C(C)C)C(C)C.[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[F:27])[NH2:23]>C(Cl)Cl>[Cl:19][C:20]1[CH:21]=[C:22]([NH:23][C:7]([C:6]2[S:5][N:4]=[N:3][C:2]=2[CH3:1])=[O:9])[CH:24]=[CH:25][C:26]=1[F:27]

Participants

5

Reactant 3

HCID 97083-Chloro-4-fluoroanilineHCID 81531DiisopropylethylamineHCID 13819924-Methyl-1,2,3-thiadiazole-5-carboxylic acid

Product 1

HCID 9077377HCID 9077377, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methyl-1,2,3-thiadiazole-5-carboxylic acid (39.6 mg, 0.275 mmol) was suspended in DCM (2.0 mL). Bromotris(pyrrolydino)phosphonium hexafluorophosphate (128 mg, 0.27 mmol) and DIPEA (96 μL, 0.55 mmol) were added and premixed for 5 minutes. 3-Chloro-4-fluoroaniline (40 mg, 0.27 mmol) was added. The solution was stirred for 3 hrs, then purified by silica gel chromatography, (Hex/EA)-eluting at ˜60% EA in hexane to afford the desired product (44 mg). MF=C10H7ClFN3OS; LCMS calculated for C10H8ClFN3OS (M+H)+: m/z=272.0.

Workup

  1. additionpremixed for 5 minutes
  2. custompurified by silica gel chromatography, (Hex/EA)-eluting at ˜60% EA in hexane

Sources & evidence

ORD record
ord-a86470a7f54f49d9968621ef680de80b
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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