4-Fluoroaniline → HCID 68681878, compound

HRID 2241619Notes

Reaction equation

HRID 2241619 reaction equation
Cl.[CH3:2][N:3]([CH3:24])[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21]([OH:23])=O)=[CH:15]3)=[O:11])[CH2:6][CH2:5]1.[F:25][B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[F:47][C:48]1C=CC(N)=CC=1.C([N:58]([CH2:62][CH3:63])[CH:59]([CH3:61])C)(C)C>CN(C)C=O>[F:25][C:48]1([F:47])[CH2:61][CH2:59][N:58]([C:21]([C:16]2[NH:17][C:18]3[C:14]([CH:15]=2)=[CH:13][C:12]([C:10]([N:7]2[CH2:8][CH2:9][CH:4]([N:3]([CH3:2])[CH3:24])[CH2:5][CH2:6]2)=[O:11])=[CH:20][CH:19]=3)=[O:23])[CH2:62][CH2:63]1

Participants

6

Reactant 4

HCID 97314-FluoroanilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68683143HCID 68683143, compound

Product 1

HCID 68681878HCID 68681878, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in analogy to example 1, from 5-(4-dimethylamino-piperidine-1-carbonyl)-1H-indole-2-carboxylic acid hydrochloride, O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (commercially available), 4-fluoroaniline (commercially available) and N,N-diisopropylethylamine in N,N-dimethylformamide, to give the desired product as a light yellow foam (72%).

Sources & evidence

ORD record
ord-41acb6562e5a4c9ab6688d007c643711
Source dataset
uspto-grants-2010_05
Patent number
US07723325B2

Reaction notes

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