4,5-Dihydrofuran-3-boronic acid pinacol ester → 3-(4,5-dihydrofuran-3-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1775084Notes

Reaction equation

HRID 1775084 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[CH:9]=2)[NH:4][N:3]=1.[O:17]1[CH2:21][CH2:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18]1>>[O:17]1[CH2:21][CH2:20][C:19]([C:2]2[C:10]3[C:5](=[CH:6][N:7]=[C:8]([C:11]4[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=4)[CH:9]=3)[NH:4][N:3]=2)=[CH:18]1

Participants

3

Reactant 2

HCID 532171654,5-Dihydrofuran-3-boronic acid pinacol esterHCID 178506572HCID 178506572, compound

Product 1

HCID 712534433-(4,5-dihydrofuran-3-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridineYield 40%

Procedure

Following the procedures Example 281, 3-iodo-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine from Example 4 and 2-(4,5-dihydrofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane were reacted to give 284 as a white solid (0.1 g, 40%). 1H NMR (400 MHz, DMSO): δ 9.42 (s, 1H), 9.09 (s, 1H), 8.56-8.57 (m, 2H), 8.51 (s, 1H), 7.86 (s, 1H), 7.47-7.49 (m, 1H), 4.46-4.50 (m, 2H), 3.12-3.14 (m, 2H). ESI MS m/z=265 (M+1)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-0a623810887e4a5995445e8df14f5bb9
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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