Sodium Bicarbonate → HCID 59251308, compound

HRID 1466429Notes

Reaction equation

HRID 1466429 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[NH:18])[C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])=[CH:4][CH:3]=1.Br[CH2:20][C:21](=O)[C:22]([CH3:28])([CH3:27])[C:23]([O:25][CH3:26])=[O:24].C([O-])(O)=O.[Na+]>C(O)(C)C>[CH3:26][O:25][C:23](=[O:24])[C:22]([C:21]1[N:18]=[C:9]([C:10]2[C:11]([Cl:17])=[CH:12][CH:13]=[CH:14][C:15]=2[Cl:16])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH:20]=1)([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 15577086Methyl 4-bromo-2,2-dimethyl-3-oxobutanoateHCID 178511965HCID 178511965, compound

Product 1

HCID 59251308HCID 59251308, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of N-(4-bromophenyl)-2,6-dichlorobenzamidine (1.03 g, 3.0 mmol), methyl 4-bromo-2,2-dimethylacetoacetate (1.78 g, 8.0 mmol) and NaHCO3 (0.76 g, 9.0 mmol) in isopropanol (12 mL) was heated in a microwave unit (Biotage Initiator™) at 170° C. for 25 min. The resulting mixture was decanted and the solids rinsed with EtOAc. The combined filtrates were concentrated and purified by chromatography (silica, EtOAc/Hex, 15:85 to 50:50) to give the title compound (0.80 g, 57%) as a pale yellow solid. 1H-NMR (DCM-d2): δ 7.44 (d, 2H), 7.27-7.34 (m, 3H), 7.09 (m, 2H), 3.67 (s, 3H), 1.61 (s, 61-1); MS (ES): 467, 469, 471 [M+H]+.

Workup

  1. customThe resulting mixture was decanted
  2. washthe solids rinsed with EtOAc
  3. concentrationThe combined filtrates were concentrated
  4. custompurified by chromatography (silica, EtOAc/Hex, 15:85 to 50:50)

Sources & evidence

ORD record
ord-2e80d5a565b54fe9b53fd5cbfd60418b
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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