4-(Pyridin-4-yl)aniline → HCID 24966320, compound

HRID 1693115Notes

Reaction equation

HRID 1693115 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[F:14][C:15]1[CH:28]=[CH:27][C:18]2[S:19][C:20]([S:23](Cl)(=[O:25])=[O:24])=[C:21]([CH3:22])[C:17]=2[CH:16]=1>ClCCl.CN(C1C=CN=CC=1)C>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:13]=[CH:12][C:10]([NH:11][S:23]([C:20]3[S:19][C:18]4[CH:27]=[CH:28][C:15]([F:14])=[CH:16][C:17]=4[C:21]=3[CH3:22])(=[O:25])=[O:24])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 15126544-(Pyridin-4-yl)anilineHCID 27745865-Fluoro-3-methylbenzo[b]thiophene-2-sulphonyl chloride

Product 1

HCID 24966320HCID 24966320, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (4-pyridine-4-yl)aniline (CAS: 13296-04-3, 0.290 g) in dichloromethane (12.0 ml) was added 5-fluoro-3-methylbenzo[b]thiophene-2-sulphonyl chloride (0.440 g) and DMAP (0.305 g). The reaction mixture was stirred at rt for 16 h, diluted with dichloromethane (12 ml) and chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain the title compound (0.205 g) as an off-white solid. MS (ISN): 397.1 (M−H)−

Workup

  1. customchromatographed on silica gel

Sources & evidence

ORD record
ord-05b769c5f1d74c3b9498256d78ee036b
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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