2-(3,4-Dihydro-2H-pyran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 5-(3,4-Dihydro-2H-pyran-5-yl)-3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1774990Notes

Reaction equation

HRID 1774990 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.[O:24]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH2:27][CH2:26][CH2:25]1>>[O:24]1[CH:25]=[C:26]([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[N:12]=4)=[N:9][N:8]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][O:19]4)[C:5]3=[CH:6][N:7]=2)[CH2:27][CH2:28][CH2:29]1

Participants

3

Reactant 2

HCID 532171522-(3,4-Dihydro-2H-pyran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 866766815-bromo-3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712537765-(3,4-Dihydro-2H-pyran-5-yl)-3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridineYield 45%

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 2-(3,4-dihydro-2H-pyran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane were reacted and purified via silica gel chromatography using a gradient of EtOAc in heptane to afford 68 mg (45%) of 5-(3,4-Dihydro-2H-pyran-5-yl)-3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine. ESI MS m/z 381.1 (M+1).

Workup

  1. customwere reacted
  2. custompurified via silica gel chromatography

Sources & evidence

ORD record
ord-39138fe482624535afc7c52f833b1622
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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