Hydrochloric Acid → (S)-(3-Bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methanamine Hydrochloride

HRID 1622558Notes

Reaction equation

HRID 1622558 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:19]1[C:24]([Br:25])=[CH:23][CH:22]=[CH:21][N:20]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)(C)(C)C.[ClH:27]>CO>[ClH:27].[Br:25][C:24]1[C:19]([C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:18])[F:16])=[CH:11][CH:10]=2)[NH2:7])=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71164782(S)-tert-butyl((3-bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate

Product 1

HCID 71144409(S)-(3-Bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methanamine HydrochlorideYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl((3-bromopyridin-2-yl)(4-(trifluoromethyl)-phenyl)methyl)carbamate (2.0 g, 4.64 mmol) in MeOH (10 mL) was added hydrogen chloride (3.48 mL, 13.91 mmol) (4.0 M in 1,4-dioxane). The reaction was then stirred for 27 h at rt under N2 and then the reaction was concentrated in vacuo to give the amine (1.7 g) as a white solid which was used without further purification in subsequent steps. MS (ESI pos. ion) m/z: 331.0, 332.9 (M+H).

Workup

  1. concentrationthe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-91f16e50f8a54d46b675e1f964f95aee
Source dataset
uspto-grants-2014_07
Patent number
US08778941B2

Reaction notes

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