4-Methoxybenzaldehyde → HCID 58268233, compound

HRID 1898228Notes

Reaction equation

HRID 1898228 reaction equation
[Br:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[Br:1][C:2]1[C:7]([NH:8][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 312444-Methoxybenzaldehyde2×HCID 516892Sodium BicarbonateHCID 27696403-Amino-2-bromo-5-chloropyridineHCID 5049666Sodium triacetoxyborohydride2×

Product 1

HCID 58268233HCID 58268233, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

5.16 g (24.8 mmol) of 2-bromo-5-chloro-pyridin-3-ylamine, 7.09 g (52.1 mmol) of p-anisaldehyde and 13.1 g (62.0 mmol) of sodium triacetoxyborohydride were dissolved in 100 mL of DCM and stirred at r.t. overnight. The next day DCM was replaced with chloroform, 5 g excess of sodium triacetoxyborohydride and 3 g excess of p-anisaldehyde were added and the reaction was conducted at 65° C. for 3 h. The mixture was worked up with aqueous sodium bicarbonate and purified on silica followed by recrystallization from ethyl acetate/hexanes mixture to give 3.40 g (42%) of the product as a white solid. MS (M+H)/z=328.9

Workup

  1. additionwere added
  2. waitthe reaction was conducted at 65° C. for 3 h
  3. custompurified on silica
  4. customfollowed by recrystallization from ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-23df9303a55a4fec99bc4b8840863a7a
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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