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Sodium Carbonate → Methyl 3-amino-2'-fluorobiphenyl-4-carboxylate

HRID 1811139
Notes
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Reaction equation

HRID 1811139 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10](Br)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[NH2:1][C:2]1[CH:11]=[C:10]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[F:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 17871390Methyl 2-Amino-4-bromobenzoate

Product 1

HCID 66605809Methyl 3-amino-2'-fluorobiphenyl-4-carboxylateYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compound
Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

Step 1 A mixture of methyl 2-amino-4-bromobenzoate (3.06 g, 13.3 mmol), 2-fluorophenylboronic acid (2.23 g, 16.0 mmol), tetrakis(triphenylphosphine)palladium (1.54 g, 1.33 mmol) and 1 M aqueous sodium carbonate (16.6 mL, 16.6 mmol) in 1,2-dimethoxyethane (66.5 mL) was stirred at 90° C. overnight. The mixture was cooled to rt, filtered through a pad of Celite and the solids were rinsed with EtOAc. The filtrate was washed with water and brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from hexane to 90:10 hexane-EtOAc) to provide methy 3-amino-2′-fluorobiphenyl-4-carboxylate (2.63 g, 81%) as a white solid. 1H NMR (400 MHz, chloroform-d) δ 7.90 (d, J=8.25 Hz, 1H), 7.38-7.46 (m, 1H), 7.27-7.35 (m, 1H), 7.08-7.22 (m, 2H), 6.85 (s, 1H), 6.82 (d, J=8.25 Hz, 1H), 5.83 (br s, 1H), 3.88 (s, 3H). Mass spectrum m/z 246.1 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through a pad of Celite
  3. washthe solids were rinsed with EtOAc
  4. washThe filtrate was washed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (
  8. washeluting with a gradient from hexane to 90:10 hexane-EtOAc)

Sources & evidence

ORD record
ord-9d5bcf7b978648a1b4e84029010a3991
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362065B2

Reaction notes

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