Toluene → HCID 5152373, compound

HRID 1069076Notes

Reaction equation

HRID 1069076 reaction equation
[CH2:1]([O:3][C:4]([C:6]1N=[C:10](Br)[CH:9]=[CH:8][CH:7]=1)=[O:5])C.[C:13](=[O:16])([O-])[O-].[Na+].[Na+].[N+](C1C=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)([O-])=O.[C:31]1(C)[CH:36]=CC=C[CH:32]=1>CO.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:13][O:16][C:26]1[CH:27]=[C:9]([C:8]2[CH:7]=[C:6]([CH:32]=[CH:31][CH:36]=2)[C:4]([O:3][CH3:1])=[O:5])[CH:10]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 2758810Ethyl 6-Bromopicolinate

Product 1

HCID 5152373HCID 5152373, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolvent

Procedure

n.m.r δ values include 1.47 (t, 2.9 H), 4.04 (s, 0.8 H), 4.50 (q, 1.46 H), 7.67 (t, 1 H), 7.97-7.99 (m, 2 H), 8.10-8.16 (m, 1 H), 8.29 (d, 1 H), 8.43-8.48 (m, 1 H), 8.86-8.87 (m, 1 H); from 2-bromo-6-pyridine-carboxylic acid ethyl ester (1.2 g) in toluene (20 mL), tetrakis(triphenylphosphine) palladium(0) (181 mg), 2 M aqueous sodium carbonate (3.3 mL) , and 3-nitrophenylboronic acid (1.0 g) in methanol (5 mL).

Sources & evidence

ORD record
ord-e02ad9befa464927873b47e70c1b0fa5
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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