4-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholine → 3-(6-Morpholinopyridin-3-yl)-1h-indazole-6-carbaldehyde

HRID 1615329Notes

Reaction equation

HRID 1615329 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[O:17])=[CH:13][CH:14]=3)[NH:9][N:8]=2)[CH:2]=1.B1(C2C=CC([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=NC=2)OC(C)(C)C(C)(C)O1>>[O:36]1[CH2:37][CH2:38][N:33]([C:6]2[N:1]=[CH:2][C:3]([C:7]3[C:15]4[C:10](=[CH:11][C:12]([CH:16]=[O:17])=[CH:13][CH:14]=4)[NH:9][N:8]=3)=[CH:4][CH:5]=2)[CH2:34][CH2:35]1

Participants

3

Reactant 2

HCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 866519663-(pyridin-3-yl)-1H-indazole-6-carbaldehyde

Product 1

HCID 875622493-(6-Morpholinopyridin-3-yl)-1h-indazole-6-carbaldehyde

Procedure

According to procedure for the synthesis of 3-(pyridin-3-yl)-1H-indazole-6-carbaldehyde, except substituting 2-(4-morpholino)pyridine-5-boronic acid pinacol ester (64 mg, 0.22 mmol), the title compound was prepared as a yellow powder (35 mg, 62%). 1H NMR (400 MHz, d6-DMSO) δ ppm 13.71 (br s, 1H), 10.14 (s, 1H), 8.77 (d, J=1.9 Hz, 1H), 8.02-8.18 (m, 2H), 8.15 (dd, J=8.9 Hz, 2.5, 1H), 7.64 (d, J=8.6 Hz, 1H), 7.00 (d, J=8.8 Hz, 1H), 3.73 (t, J=4.5 Hz, 4H), 3.53 (t, J=5.1 Hz, 4H); MS ESI 309.1 (100) [M+H]+, calcd for [C17H16N4O2+H]+ 309.13.

Sources & evidence

ORD record
ord-142e0a0e86054b5686ec23cd1159cd5c
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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