2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile → 2-{4-[6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-3-yl]-1H-pyrazol-1-yl}propanenitrile

HRID 1778702Notes

Reaction equation

HRID 1778702 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19](I)=[N:20][NH:21][C:15]=2[CH:14]=1.CC1(C)C(C)(C)OB([C:31]2[CH:32]=[N:33][N:34]([CH:36]([CH3:39])[C:37]#[N:38])[CH:35]=2)O1>>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19]([C:31]3[CH:32]=[N:33][N:34]([CH:36]([CH3:39])[C:37]#[N:38])[CH:35]=3)=[N:20][NH:21][C:15]=2[CH:14]=1

Participants

3

Reactant 2

HCID 867228232-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrileHCID 1784934546-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 762853632-{4-[6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-3-yl]-1H-pyrazol-1-yl}propanenitrile

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 4, Step 2 starting from 6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridine and 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propanenitrile. LCMS (M+H)+=443.0/445.0. 1H NMR (300 MHz, DMSO-d6) δ: 9.39 (s, 1H), 8.66 (s, 1H), 8.27 (s, 1H), 7.42 (s, 1H), 7.00 (s, 1H), 5.91 (q, J=7.1 Hz, 1H), 3.96 (s, 6H), 1.88 (d, J=7.1 Hz, 3H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-7327cdb0bbc74a0b86c1a0f3d3daec94
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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