6-Bromo-7-methylquinoline → (7-Methyl-quinolin-6-yl)-acetic acid tert-butyl ester

HRID 655225Notes

Reaction equation

HRID 655225 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[N:8]=[CH:7][CH:6]=[CH:5]2.[C:13]([O-:16])(=[O:15])[CH3:14].[Br-].[C:18]([Zn+2])([CH3:21])([CH3:20])[CH3:19]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([O:15][C:13](=[O:16])[CH2:14][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[N:8]=[CH:7][CH:6]=[CH:5]2)([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 579110186-Bromo-7-methylquinolineHCID 178476297HCID 178476297, compound

Product 1

HCID 68703613(7-Methyl-quinolin-6-yl)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To 1.02 g of 6-bromo-7-methyl-quinoline were added a solution of 20 ml of tert-butylzincbromide acetate and 0.58 g of Pd(PPh3)4. The mixture was placed in the microwave reactor for 30 min to achieve a temperature of 120° C. (repeated for 3 times.). Purification via flash column chromatography returned the title compound (3.2 g, 68%). 1H NMR (CDCl3, 300 MHz) δ 8.84 (m, 1H), 8.07 (m, 1H), 7.89 (s, 1H), 7.63 (s, 1H), 7.31 (m, 1H), 3.72 (s, 2H), 2.51 (s, 3H), 1.46 (s, 9H).

Workup

  1. customa temperature of 120° C. (repeated for 3 times.)
  2. customPurification via flash column chromatography

Sources & evidence

ORD record
ord-f3c40efb057f4c2f910e79ed9dd3a108
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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