1-Naphthaleneboronic acid → HCID 86720518, compound

HRID 1054093Notes

Reaction equation

HRID 1054093 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=1.[C:10]1(B(O)O)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1>>[C:18]1([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=2)[C:19]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 2545321-Naphthaleneboronic acidHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 86720518HCID 86720518, compound

Procedure

Synthesized using compound 43c (720 mg, 3.87 mmol) and 1-naphthaleneboronic acid (1.00 g, 5.81 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (8:1) as eluent. Orange solid. Yield: 733 mg, 81%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=7.50-7.62 (m, 3H), 7.65-7.69 (m, 1H), 7.77-7.81 (m, 1H), 7.92-8.00 (m, 2H), 8.10-8.14 (m, 1H), 8.31 (dd, J=7.9, 2.2 Hz, 1H), 9.25 (dd, J=2.2, 0.9 Hz, 1H), 10.22 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=125.1, 125.2, 125.4, 126.2, 127.0, 128.0, 128.5, 129.7, 130.0, 130.7, 134.0, 136.1, 137.2, 152.1, 164.6, 190.5; MS (ESI): m/z=234.29 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (8:1) as eluent

Sources & evidence

ORD record
ord-1d91bb45b3884f02975479e226baa5cb
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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