5-Fluoro-2-methoxyphenylboronic acid → HCID 23433509, compound

HRID 1279962Notes

Reaction equation

HRID 1279962 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6](C2C(C(OC)=O)=CC([N+]([O-])=O)=CC=2)[CH:7]=1.Br[C:24]1[C:33]([CH3:34])=[CH:32][C:31]([N+:35]([O-:37])=[O:36])=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27].FC1C=CC(OC)=C(B(O)O)C=1>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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[CH:6][C:7]=1[C:24]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][C:31]([N+:35]([O-:37])=[O:36])=[CH:32][C:33]=1[CH3:34]

Participants

5

Reactant 3

HCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 10733357Methyl5'-fluoro-2'-methoxy-4-nitro-2-biphenylcarboxylateHCID 23433653Methyl 2-bromo-3-methyl-5-nitrobenzoate

Product 1

HCID 23433509HCID 23433509, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

This compound was prepared in a manner similar to that of methyl 5′-Fluoro-2′-methoxy-4-nitro-2-biphenylcarboxylate (EXAMPLE 107) from methyl 2-bromo-3-methyl-5-nitrobenzoate (1.73 g, 6.31 mmol), (PPh3)4Pd (0.22 g, 0.19 mmol), and 5-Fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) (1.50 g, 8.8 mmol) to afford 0.77 g (38%) of methyl 2′-Fluoro-5′-methoxy-6-methyl-4-nitro-2-biphenylcarboxylate. Data for 2′-Fluoro-5′-methoxy-6-methyl-4-nitro-2-biphenylcarboxylate: 8.61 (d, J=2.3, 1H), 8.27 (d, J=2.4, 1H), 7.09 (m, 1H), 6.91 (dd, J=9.0, 4.3, 1H), 6.73 (dd, J=8.2, 3.0, 1H), 3.70 (s, 3H), 3.69 (s, 3H), 2.19 (s, 3H).

Sources & evidence

ORD record
ord-5c8475b330c2490899f6ebeb66172750
Source dataset
uspto-grants-2002_09
Patent number
US06448405B1

Reaction notes

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