1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 4-Methoxy-3-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 1046501Notes

Reaction equation

HRID 1046501 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:12]3[C:13]([O:17][CH3:18])=[N:14][CH:15]=[CH:16][C:11]=3[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:38][N:39]1[CH:43]=[C:42](B2OC(C)(C)C(C)(C)O2)[CH:41]=[N:40]1>>[CH3:18][O:17][C:13]1[C:12]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([C:42]4[CH:41]=[N:40][N:39]([CH3:38])[CH:43]=4)[CH:7]=3)=[N:9][NH:10][C:11]=2[CH:16]=[CH:15][N:14]=1

Participants

3

Reactant 2

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 866736973-(2-Chloropyridin-4-yl)-4-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 569429864-Methoxy-3-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)-1H-pyrazolo[4,3-c]pyridineYield 57%

Procedure

Prepared according to the procedure described in Example 116, by reacting 3-(2-chloropyridin-4-yl)-4-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine with 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole to give the title compound (30.5 mg, 57% over two steps). LC-MS (Method G): m/z=307.0 (M+H)+; 3.06 min. 1H-NMR (400 MHz, DMSO): δ 13.89 (br s, 1H), 8.60 (d, J=5.2, 1H), 8.34 (s, 1H), 8.22 (s, 1H), 8.03 (s, 1H), 7.97 (d, J=6.0, 1H), 7.75 (dd, J=5.2, 1.5 Hz, 1H), 7.23 (d, J=6.0, 1H), 4.05 (s, 3H), 3.91 (s, 3H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-61fd3084480d44bb80526d80424f072a
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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