Methyl 4-Formylbenzoate → HCID 89601758, compound

HRID 526301Notes

Reaction equation

HRID 526301 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[CH2:11][N:12]([CH3:15])[CH2:13][CH2:14][C:3]=12.[Li]C(C)(C)C.[CH:21]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)=[O:22]>CCOCC>[OH:22][CH:21]([C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[CH2:11][N:12]([CH3:15])[CH2:13][CH2:14][C:3]=12)[C:23]1[CH:24]=[CH:25][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 89601845HCID 89601845, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 89601758HCID 89601758, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-bromo-2-methyl-1,2,3,4-tetrahydropyrimido[1,6-a]indole (0.254 g) in 8 mL of ether cooled at −78° C. was added t-BuLi (1.4 mL, 1.7 M in pentane) dropwise. After attiring at −78° C. for 15 min, a solution of methyl 4-formylbenzoate (0.200 g in 2 mL of ether) was added quickly by a syringe. The reaction mixture was wormed to r.t. over 10 min, and quenched with 10 mL of saturated aqueous solution of NH4Cl, and 20 mL of EtOAc was added. The solid was collected by filtration to give 0.2 g of the title compound as a white solid.

Workup

  1. waitThe reaction mixture was wormed to r.t. over 10 min
  2. customquenched with 10 mL of saturated aqueous solution of NH4Cl, and 20 mL of EtOAc
  3. additionwas added
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-dee97eb88090457e83d3798bfcb18faa
Source dataset
uspto-grants-2016_05
Patent number
US09345905B2

Reaction notes

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