Water → 5-Bromo-6-(cyclopropylmethoxy)-3-pyridinamine

HRID 1958098Notes

Reaction equation

HRID 1958098 reaction equation
[Br:1][C:2]1[C:3]([O:11][CH2:12][CH:13]2[CH2:15][CH2:14]2)=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.O.[Cl-].[NH4+]>CO.ClCCl.[Zn]>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[N:4][C:3]=1[O:11][CH2:12][CH:13]1[CH2:15][CH2:14]1

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 67281724HCID 67281724, compound

Product 1

HCID 672819095-Bromo-6-(cyclopropylmethoxy)-3-pyridinamineYield 95.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-bromo-2-cyclopropylmethoxy-5-nitro-pyridine (600 mg, 2.19 mmol) in methanol (30 ml) were added water (15 ml), zinc dust (1 g, 15.37 mmol) and ammonium chloride (1.28 g, 24.09 mmol) at 25° C., and the reaction mixture was stirred for 45 min at 25° C. After total consumption of starting material (monitored by TLC), the reaction mixture was filtered through a bed of celite, and the filtrate was evaporated under reduced pressure to get the crude residue. The residue was dissolved in dichloromethane and washed with water and brine. The organic part was dried over Na2SO4 and evaporated to get the compound (507 mg, 95%). This compound was used in next step without further purification. MS (LC/MS): 244.0 (M+H).

Workup

  1. customAfter total consumption of starting material (monitored by TLC)
  2. filtrationthe reaction mixture was filtered through a bed of celite
  3. customthe filtrate was evaporated under reduced pressure
  4. customto get the crude residue
  5. washwashed with water and brine
  6. dry with materialThe organic part was dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-24cb535b7d0246bfb115a4fee89e773d
Source dataset
uspto-grants-2013_04
Patent number
US08410107B2

Reaction notes

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