1-(Ethoxycarbonylmethyl)-1H-pyrazole-4-boronic acid pinacol ester → Ethyl 2-(4-(3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)acetate

HRID 1775004Notes

Reaction equation

HRID 1775004 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[N:12]=3)=[N:9][N:8]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)[C:5]2=[CH:6][N:7]=1.CC1(C)C(C)(C)OB([C:32]2[CH:33]=[N:34][N:35]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:36]=2)O1>>[F:17][C:13]1[N:12]=[C:11]([C:10]2[C:4]3[C:5](=[CH:6][N:7]=[C:2]([C:32]4[CH:33]=[N:34][N:35]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:36]=4)[CH:3]=3)[N:8]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)[N:9]=2)[CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 162183851-(Ethoxycarbonylmethyl)-1H-pyrazole-4-boronic acid pinacol esterHCID 866766815-bromo-3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 71253737Ethyl 2-(4-(3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)acetateYield 56%

Procedure

Following the Suzuki coupling procedure of Example 10, 5-bromo-3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine and ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)acetate, were reacted and purified via silica gel chromatography using a gradient of EtOAc in heptane to afford 100 mg (56%) of Ethyl 2-(4-(3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)acetate. ESI MS m/z 451.1 (M+1).

Workup

  1. customwere reacted
  2. custompurified via silica gel chromatography

Sources & evidence

ORD record
ord-f48db92098a8478db56c6e4c0b0c5afa
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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