(Naphthalen-2-yl)boronic acid → HCID 57329709, compound

HRID 1054060Notes

Reaction equation

HRID 1054060 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.[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:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)=[N:24][CH:25]=2)[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

3

Reactant 2

HCID 2734375(Naphthalen-2-yl)boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 57329709HCID 57329709, compound

Procedure

Synthesized using 2-naphthylboronic acid (217 g, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 118 mg, 0.41 mmol, 66%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 5.23 (s, 2H), 6.97 (s, 1H), 7.17 (s, 1H), 7.50-7.53 (m, 2H), 7.57 (dd, J=8.2, 2.4 Hz, 1H), 7.85-7.88 (m, 3H), 7.95 (d, J=8.8 Hz, 2H), 8.11 (dd, J=8.5, J=1.8 Hz, 1H), 8.47 (d, J=0.9 Hz, 1H), 8.65 (d, J=1.8 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.4, 119.2, 120.9, 124.3, 126.4, 126.5, 126.8, 127.7, 128.6, 128.7, 129.3, 129.8, 133.4, 133.8, 135.7, 136.0, 137.2, 148.7; MS (ESI): m/z=285.92 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-cd2c20c7205b4a84b954c976fa4f5793
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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