2-Bromo-6-fluoropyridine → 1-(6-(2,6-Diazaspiro[3.3]heptan-2-yl)pyridin-2-yl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 57991Notes

Reaction equation

HRID 57991 reaction equation
[CH2:1]1[C:4]2([CH2:7][NH:6][CH2:5]2)[CH2:3][N:2]1[C:8](OC(C)(C)C)=O.BrC1[CH:21]=[CH:20][CH:19]=[C:18](F)[N:17]=1.Cl[C:24]1[N:29]=[CH:28][C:27]2[CH:30]=[N:31][NH:32][C:26]=2[CH:25]=1.[CH3:33][N:34]1[CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:36]=[N:35]1>>[CH2:3]1[C:4]2([CH2:5][NH:6][CH2:7]2)[CH2:1][N:2]1[C:8]1[N:17]=[C:18]([N:32]2[C:26]3[CH:25]=[C:24]([C:37]4[CH:36]=[N:35][N:34]([CH3:33])[CH:38]=4)[N:29]=[CH:28][C:27]=3[CH:30]=[N:31]2)[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 4

HCID 6394382-Bromo-6-fluoropyridineHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 401519812-Boc-2,6-diazaspiro(3.3)heptaneHCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridine

Product 1

HCID 867071761-(6-(2,6-Diazaspiro[3.3]heptan-2-yl)pyridin-2-yl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridineYield 26%

Procedure

Following the procedures as described in Example 124 and starting with tert-butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate, 2-bromo-6-fluoropyridine, 6-chloro-1H-pyrazolo[4,3-c]pyridine, and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 268 was obtained as a yellow solid (87 mg, 26%) over four steps. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.10 (s, 1H), 8.74 (s, 1H), 8.51 (s, 1H), 8.28 (s, 1H), 7.98 (s, 1H), 7.69-7.71 (t, J=9 Hz, 1H), 7.20-7.21 (d, J=9 Hz, 1H), 6.30-6.31 (d, J=9 Hz, 1H), 4.24 (s, 3H), 4.08 (s, 1H), 3.86-3.93 (m, 3H), 3.79-3.83 (m, 2H), 3.35-3.42 (m, 3H); MS (ESI) m/z: 373 [M+H]+.

Sources & evidence

ORD record
ord-715f93269670434eaccad8f79b370924
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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