3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 71254131, compound

HRID 1775052Notes

Reaction equation

HRID 1775052 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10](I)=[N:9][N:8](C3CCCCO3)[C:5]2=[CH:6][N:7]=1.[C:18]([C:20]1[CH:21]=[C:22]([N:35]2[CH2:40][CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37][CH2:36]2)[CH:23]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:25]=1)#[N:19].[N:48]1[CH:53]=[CH:52][CH:51]=[C:50](B2OC(C)(C)C(C)(C)O2)[CH:49]=1>>[N:35]1([C:22]2[CH:21]=[C:20]([CH:25]=[C:24]([C:10]3[C:4]4[C:5](=[CH:6][N:7]=[C:2]([C:50]5[CH:49]=[N:48][CH:53]=[CH:52][CH:51]=5)[CH:3]=4)[NH:8][N:9]=3)[CH:23]=2)[C:18]#[N:19])[CH2:36][CH2:37][NH:38][CH2:39][CH2:40]1

Participants

4

Reactant 3

HCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 59588112HCID 59588112, compoundHCID 726984825-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 71254131HCID 71254131, compoundYield 19%

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 tert-butyl 4-(3-cyano-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylate were reacted. The product was coupled with 3-pyridineboronic acid pinacol ester by the Suzuki coupling procedure of Example 10 and deprotected by the procedure of Example 225. The mixture was purified via reverse phase HPLC using a gradient of MeOH in water with 0.1% NH4OH to afford 37 mg (19%) of 240 over three steps. ESI MS m/z 382.2 (M+1). 1H NMR (400 MHz, DMSO): 9.41 (s, 1H), 9.23 (s, 1H), 8.68-8.59 (m, 2H), 8.55 (d, J=7.8 Hz, 1H), 7.87 (s, 1H), 7.80 (s, 1H), 7.56-7.50 (m, 1H), 7.43 (s, 1H), 3.26-3.23 (m, 4H), 2.87-2.81 (m, 4H)

Workup

  1. customwere reacted
  2. customThe mixture was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-efbb8244c4144c3fb34c99e0e106eef6
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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