Ethyl Acetate → HCID 22392809, compound

HRID 1071388Notes

Reaction equation

HRID 1071388 reaction equation
[CH3:1][C:2]1(B(O)OC(O)=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH2:3]1.BrC1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([CH3:25])[CH:16]=1.[C:26]([O-])([OH:28])=[O:27].[Na+].CCOC(C)=O>C1COCC1.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>[CH3:25][C:17]1[CH:16]=[C:1]([C:2]2[CH:3]=[CH:4][C:5]([C:26]([OH:28])=[O:27])=[CH:6][CH:7]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 155606774-Bromo-2-methylquinolineHCID 68893156HCID 68893156, compound

Product 1

HCID 22392809HCID 22392809, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To 1-methylcarboxyphenylboronic acid (1.0 g, 5.6 mmol) and 4-bromo-2-methylquinoline (1.24 g, 5.6 mmol) in THF/aq K2CO3 was added Pd(PPh3)4 and the reaction was heated to 70° C. for 16 hr. Aqueous workup using NaHCO3 and EtOAc, column chromatography and saponification using the same conditions as for Example 214 gave the final product. MS found: (M+H)=264.

Sources & evidence

ORD record
ord-575210d8efad421b99d4702a80f84cd9
Source dataset
uspto-grants-2005_06
Patent number
US06906053B2

Reaction notes

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