Isoquinoline-4-boronic acid → HCID 67516370, compound

HRID 1054065Notes

Reaction equation

HRID 1054065 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](B(O)O)=[CH:3][N: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:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=[N:2][CH:3]=3)=[N:24][CH:25]=2)[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

3

Reactant 2

HCID 3761204Isoquinoline-4-boronic acidHCID 706809855-((1H-imidazol-1-yl)methyl)-2-bromopyridine

Product 1

HCID 67516370HCID 67516370, compound

Procedure

Synthesized using 4-isoquinolinylboronic acid (218 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 97 mg, 0.34 mmol, 54%. 1H NMR (CDCl3, 500 MHz): δH (ppm): 5.26 (s, 2H), 7.00 (t, J=1.3 Hz, 1H), 7.16 (brs, 1H), 7.58-7.66 (m, 4H), 7.70-7.73 (m, 1H), 8.04 (d, J=8.2 Hz, 1H), 8.17 (dd, J=8.5, 0.6 Hz, 1H), 8.62 (s, 1H), 8.71 (d, J=1.6 Hz, 1H), 9.30 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.1, 119.1, 124.5, 125.0, 127.4, 128.0, 128.5, 130.0, 130.4, 130.8, 131.1, 133.6, 135.7, 137.4, 143.5, 148.5, 153.4, 156.6; MS (ESI): m/z=287.10 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-c6b7cda493004c09b507180005116395
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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