Trifluoroborane Hydrofluoride → ethyl 4-fluoro-2-{[(1S,2S)-2-pyrrolidin-1-ylcyclohexyl]amino}benzoate

HRID 425978Notes

Reaction equation

HRID 425978 reaction equation
N[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([NH:13][C@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@@H:15]2[N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:3]=1.N([O-])=O.[Na+].[F:29]B(F)F.F>O>[F:29][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([NH:13][C@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@@H:15]2[N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:3]=1

Participants

5

Reactant 3

HCID 9855450Trifluoroborane HydrofluorideHCID 23668193Sodium NitriteHCID 66703696ethyl 4-amino-2-{[(1S,2S)-2-pyrrolidin-1-ylcyclohexyl]amino}benzoate

Product 1

HCID 66703633ethyl 4-fluoro-2-{[(1S,2S)-2-pyrrolidin-1-ylcyclohexyl]amino}benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 4-amino-2-{[(1S,2S)-2-pyrrolidin-1-ylcyclohexyl]amino}benzoate was allowed to react with sodium nitrite (NaNO2) and trifluoroborane-hydrogen fluoride complex (BF3.HF) in water at 10° C. for 10 minutes. By post-treating the reaction liquid, ethyl 4-fluoro-2-{[(1S,2S)-2-pyrrolidin-1-ylcyclohexyl]amino}benzoate was obtained.

Workup

  1. additionBy post-treating
  2. customthe reaction liquid

Sources & evidence

ORD record
ord-ffce739e005243c882101ec59ef75aed
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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