3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 71253722, compound

HRID 1775036Notes

Reaction equation

HRID 1775036 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10](I)=[N:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:5]2=[CH:6][N:7]=1.[C:18]1(B2OC(C)(C)C(C)(C)O2)[CH2:22][CH2:21][CH2:20][CH:19]=1.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=1>>[C:18]1([C:10]2[C:4]3[C:5](=[CH:6][N:7]=[C:2]([C:34]4[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=4)[CH:3]=3)[N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:9]=2)[CH2:22][CH2:21][CH2:20][CH:19]=1

Participants

4

Reactant 3

HCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 154866112-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 726984825-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 71253722HCID 71253722, compoundYield 61%

Procedure

Following the Suzuki coupling procedure of Example 159, 5-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine and 2-cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane were reacted. The product was reacted with 3-pyridineboronic acid pinacol ester by the Suzuki coupling procedure of Example 10 and the mixture was purified via silica gel chromatography using a gradient of ethyl acetate in heptane to afford 106 mg (61%) of 3-Cyclopentenyl-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine over two steps. ESI MS m/z 347.3 (M+1).

Workup

  1. customwere reacted
  2. customthe mixture was purified via silica gel chromatography

Sources & evidence

ORD record
ord-179f795f39494b1ba7096c75922696d1
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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