Trimethylsilyldiazomethane → Methyl 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinate

HRID 494699Notes

Reaction equation

HRID 494699 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([C:22]([OH:24])=[O:23])=[CH:20][N:19]=[C:18]([Cl:25])[C:17]=2[Cl:26])=[C:11]([Cl:27])[CH:10]=1>>[CH3:1][O:23][C:22](=[O:24])[C:21]1[C:16]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([Br:8])=[CH:10][C:11]=2[Cl:27])=[C:17]([Cl:26])[C:18]([Cl:25])=[N:19][CH:20]=1

Participants

3

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 116612174-(4-Bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid

Product 1

HCID 11603943Methyl 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinate

Procedure

Trimethylsilyldiazomethane (2.0 M solution in hexanes, 37 mL, 74 mmol) was added slowly to a suspension of 4-(4-bromo-2-chloro-phenylamino)-5,6-dichloronicotinic acid (25) (14.67 g, 37 mmol). After the addition was complete the resulting slurry was diluted with hexanes (600 mL) and the solids isolated by filtration washing with hexanes. The desired product was isolated as an off-white solid (10.06 g). The hexanes washes were concentrated and the solids passed through a plug of silica gel eluting with dichloromethane. Concentration of the product-containing fractions provided an additional 3.83 g desired product (26) for a total of 13.89 g (91%). MS (APCI+) m/z 409, 411, 413 (M+; Cl, Br pattern) detected.

Workup

  1. additionAfter the addition
  2. customthe solids isolated by filtration
  3. washwashing with hexanes

Sources & evidence

ORD record
ord-6fe8e9e83bf348dabf503864759440da
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

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