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

HRID 509329Notes

Reaction equation

HRID 509329 reaction equation
[Br:1][C:2]1[C:3]([C@@H:8]([NH:19]C(=O)OC(C)(C)C)[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[ClH:27]>CO>[ClH:27].[Br:1][C:2]1[C:3]([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)[NH2:19])=[N:4][CH:5]=[CH:6][CH:7]=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 Hydrochloride

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 stirred for 27 h at rt under N2. The reaction was concentrated in vacuo to give the amine 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-b1df8c822a724351b799e5aadb10e9ed
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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