3-Fluorophenylboronic acid → HCID 59654732, compound

HRID 2053244Notes

Reaction equation

HRID 2053244 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2[O:15][C:16](Br)=[CH:17][CH:18]=2)=[O:13])[CH:6]=1.[F:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1>>[F:21][C:22]1[CH:27]=[C:26]([C:16]2[O:15][C:14]([C:12]([NH:11][C:7]3[CH:6]=[C:5]([CH2:4][C:3]([OH:2])=[O:20])[CH:10]=[CH:9][CH:8]=3)=[O:13])=[CH:18][CH:17]=2)[CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 27339863-Fluorophenylboronic acidHCID 59654700(3-[(5-Bromo-furan-2-carbonyl)-amino]-phenyl)-acetic Acid Methyl Ester

Product 1

HCID 59654732HCID 59654732, compound

Procedure

The furyl bromide (16)(100 mg, 0.30 mmol) was coupled to 3-fluoro-phenylboronic acid (42 mg, 0.30 mmol) using Method E. During this reaction, hydrolysis occurred. The residue was extracted using Work-up E1 to give the title compound. Yield: 26 mg, 25%; LC/MS tr 1.45 min; MS(ES+) m/z 339 (M+H); HPLC Purity: 91%; 1H NMR (400 MHz; DMSO): δ 3.50 (s, 2H), 6.95 (d, 1H), 7.15 (t, 1H), 7.20 (d, 1H), 7.24 (t, 1H), 7.32 (d, 1H), 7.46 (q, 1H), 7.56 (s, 1H), 7.62 (d, 1H), 7.74 (d, 1H), 7.83 (d, 1H), 10.13 (s, 1H)

Workup

  1. customDuring this reaction, hydrolysis
  2. extractionThe residue was extracted

Sources & evidence

ORD record
ord-1cde64b621094d6296c087a7b00d47a8
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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