Ammonium Acetate → 1-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanamine

HRID 2274116Notes

Reaction equation

HRID 2274116 reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:10](=O)[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].C([O-])(=O)C.[NH4+].C([BH3-])#[N:21].[Na+]>C(#N)C.CO>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH:10]([NH2:21])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 866669121-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanone

Product 1

HCID 866669161-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanamineYield 23%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanone (0.44 g, 1.6 mmol) and ammonium acetate (1.8 g, 23 mmol) in acetonitrile (3.0 mL) and methanol (3.0 mL) was heated at 65° C. for an hour. Sodium cyanoborohydride (0.244 g, 3.88 mmol) was added and the mixture was heated at 65° C. overnight. Purification by preparative LCMS (pH=10) gave the desired compound (23% yield). LCMS calculated for C9H8BrClFO (M−NH2)+: m/z=264.9, 266.9. found: 264.9, 266.9. 1H NMR (300 MHz, CDCl3): δ 8.81 (br s, 2H), 7.80 (s, 1H), 4.80 (m, 1H), 3.97 (s, 3H), 1.69 (m, 3H).

Workup

  1. temperaturethe mixture was heated at 65° C. overnight
  2. customPurification by preparative LCMS (pH=10)

Sources & evidence

ORD record
ord-635eafa529714de08d49e1008ca9108c
Source dataset
uspto-grants-2015_09
Patent number
US09126948B2

Reaction notes

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