Hydrogen Bromide → 4-Chloro-3-iodopyridin-2-amine

HRID 1046004Notes

Reaction equation

HRID 1046004 reaction equation
Br.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9]C(=O)OC(C)(C)C)[C:4]=1[I:17].[OH-].[Na+]>O>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[C:4]=1[I:17]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 59852886tert-Butyl (4-chloro-3-iodopyridin-2-yl)carbamate

Product 1

HCID 229365964-Chloro-3-iodopyridin-2-amineYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of aqueous HBr (48%, 10 mL, 13.26 mmol) was added to tert-butyl (4-chloro-3-iodopyridin-2-yl)carbamate (4.7 g, 13.26 mmol) and the suspension was stirred at RT for 3 h. The reaction mixture was diluted with water (40 ml), basified with 2N NaOH and the resultant suspension was filtered, washed with water (4×1 mL) and dried to afford 4-chloro-3-iodopyridin-2-amine as white solid (3.05 g, 90% yield). MS (ESI) m/z: 254.9 (M+H+).

Workup

  1. filtrationthe resultant suspension was filtered
  2. washwashed with water (4×1 mL)
  3. customdried

Sources & evidence

ORD record
ord-399d47f5fba5491899c37c1490d9db8f
Source dataset
uspto-grants-2013_10
Patent number
US08569319B2

Reaction notes

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