Potassium Carbonate → HCID 10638416, compound

HRID 2121260Notes

Reaction equation

HRID 2121260 reaction equation
Br[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:15]1(B(O)O)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.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>[N+:12]([C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([C:23]2[C:24]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:20]=[CH:21][CH:22]=2)[CH:11]=1)([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 15833211Methyl 2-Bromo-4-nitrobenzoate

Product 1

HCID 10638416HCID 10638416, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Methyl 2-bromo-4-nitrobenzoate (3.86 g, 14.85 mmol) was coupled with 1-naphthylboronic acid (3.06 g, 17.79 mmol) in DMF in the presence of K2CO3 (3.0 eq) and Pd(PPh3)4 (0.03 eq) at 110° C. for 15 hrs. After flash column chromotography purification, the desired compound was obtained as a pale yellow oil (3.86 g, yield 85%). 1H NMR (CDCl3) δ 8.34 (d, J=8.5 Hz, 1H), 8.28 (s, 1H), 8.14 (d, J=8.5 Hz, 1H), 7.92 (m, 2H), 7.47-7.56 (m, 2H), 7.41 (d, J=3.8 Hz, 2H), 7.34 (d, J=6.8 Hz, 1H), 3.40 (s, 3H); 13C NMR (CDCl3) δ 166.4, 149.2, 142.7, 137.2, 136.8, 133.2, 131.3, 131.0, 128.6, 128.4, 126.6, 126.2, 126.0, 125.0, 124.7, 122.3, 52.3.

Workup

  1. customAfter flash column chromotography purification

Sources & evidence

ORD record
ord-911c291f88ff4d8893b3defc06c55e48
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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