5-Chlorothiophene-2-boronic acid → HCID 67511528, compound

HRID 1054068Notes

Reaction equation

HRID 1054068 reaction equation
[Cl:1][C:2]1[S:6][C:5](B(O)O)=[CH:4][CH:3]=1.[N:10]1([CH2:15][C:16]2[CH:17]=[CH:18][C:19](Br)=[N:20][CH:21]=2)[CH:14]=[CH:13][N:12]=[CH:11]1>>[Cl:1][C:2]1[S:6][C:5]([C:19]2[CH:18]=[CH:17][C:16]([CH2:15][N:10]3[CH:14]=[CH:13][N:12]=[CH:11]3)=[CH:21][N:20]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27343245-Chlorothiophene-2-boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 67511528HCID 67511528, compound

Procedure

Synthesized using 5-chloro-2-thiophenylboronic acid (205 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 83 mg, 0.30 mmol, 47%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 5.17 (s, 2H), 6.91-6.92 (m, 2H), 7.13 (s, 1H), 7.33 (d, J=4.0 Hz, 1H), 7.46 (dd, J=8.2, 2.1 Hz, 1H), 7.55 (d, J=8.2 Hz, 1H), 7.80 (s, 1H), 8.42 (d, J=1.5 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.3, 118.16, 119.1, 124.2, 127.3, 129.5, 129.8, 133.1, 135.9, 137.2, 142.5, 148.5, 152.1; MS (ESI): m/z=275.98 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-d3056df8f14a4b579ecd53309b281bea
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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