1-Naphthaleneboronic acid → HCID 53475401, compound

HRID 1054059Notes

Reaction equation

HRID 1054059 reaction equation
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[N:14]1([CH2:19][C:20]2[CH:21]=[CH:22][C:23](Br)=[N:24][CH:25]=2)[CH:18]=[CH:17][N:16]=[CH:15]1>>[N:14]1([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)=[N:24][CH:25]=2)[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

3

Reactant 2

HCID 2545321-Naphthaleneboronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 53475401HCID 53475401, compound

Procedure

Synthesized using 1-naphthylboronic acid (217 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 130 mg, 0.46 mmol, 72%. 1H NMR (500 MHz, CDCl3): δH (ppm): 5.25 (s, 2H), 7.00 (t, J=1.3 Hz, 1H), 7.16 (t, J=1.3 Hz, 1H), 7.46-7.52 (m, 2H), 7.54-7.60 (m, 4H), 7.65 (br, s, 1H), 7.90-7.93 (m, 2H), 8.03-8.05 (m, 1H), 8.70 (dd, J=2.5, 0.9 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.19, 119.1, 125.2, 125.2, 125.3, 126.0, 126.6, 127.6, 128.4, 129.2, 130.1, 130.3, 131.0, 135.3, 137.3, 137.6, 148.3, 159.5; MS (ESI): m/z=286.05 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-a3aa84106d3b4e2d9501b74c6cc1f0cf
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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