23138-53-6 → Methyl 4-(4-chloro-3-isopropoxy-5-methoxybenzamido)benzoate

HRID 62769Notes

Reaction equation

HRID 62769 reaction equation
C([Li])CCC.[Cl:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10](I)=[CH:9][C:8]=1[O:16][CH:17]([CH3:19])[CH3:18].[N:20]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)=[C:21]=[O:22]>C1COCC1>[Cl:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([C:21]([NH:20][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)=[O:22])=[CH:9][C:8]=1[O:16][CH:17]([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 28045423138-53-6HCID 67041857HCID 67041857, compoundHCID 178418339Butyllithium

Product 1

HCID 67041570Methyl 4-(4-chloro-3-isopropoxy-5-methoxybenzamido)benzoateYield 6.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (364 μl, 0.909 mmol) was slowly added to a solution of 2-chloro-5-iodo-1-isopropoxy-3-methoxybenzene (3) (270 mg, 0.827 mmol) in anhydrous THF (5 mL) at −78° C. After stirring for 15 min at this temperature a solution of methyl 4-isocyanatobenzoate (176 mg, 0.992 mmol) in anhydrous THF (5 mL) was added dropwise. The solution was allowed to warm to RT and stirred for a further 20 h. The reaction mixture was partitioned between DCM (40 mL) and brine (100 mL). The phases were separated and the organic solution was dried over MgSO4, filtered and the solvent was removed in vacuo. The residue was purified by silica gel chromatography (40 g, 0-40% EtOAc in isohexane) to afford methyl 4-(4-chloro-3-isopropoxy-5-methoxybenzamido)benzoate (5) (20 mg, 6%) as a colourless oil: m/z 376 [M−H]− (ES−).

Workup

  1. additionwas added dropwise
  2. customThe reaction mixture was partitioned between DCM (40 mL) and brine (100 mL)
  3. customThe phases were separated
  4. dry with materialthe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by silica gel chromatography (40 g, 0-40% EtOAc in isohexane)

Sources & evidence

ORD record
ord-b5154fa4399c4b45b1e11a47d77516ed
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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