HCID 66851324, compound → HCID 66851628, compound

HRID 1466656Notes

Reaction equation

HRID 1466656 reaction equation
[CH3:1][O:2][C:3]1[C:10]([C:11]2[N:15]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:14]=[CH:13][C:12]=2[N+:24]([O-])=O)=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1>CO.[Pd]>[NH2:24][C:12]1[CH:13]=[N:14][N:15]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:23])[CH3:22])[C:11]=1[C:10]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

4

Reactant 1

HCID 66851324HCID 66851324, compound

Product 1

HCID 66851628HCID 66851628, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6-methoxy-5-(4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)nicotinonitrile (11 mg, 0.029 mmol, 1 equiv) in methanol (4 mL) was circulated through a H-Cube® continuous-flow hydrogenation reactor (ThalesNano) fitted with a palladium on carbon catalyst cartridge at 30° C. The resulting solution was concentrated in vacuo to provide product (7.1 mg, 70% crude yield). 1H NMR (400 MHz, CDCl3), δ: 8.52 (d, J=2.2 Hz, 1H), 8.09 (d, J=2.2 Hz, 1H), 5.21 (s, 2H), 4.06 (s, 3H), 3.58 (m, 2H), 0.85 (m, 2H), −0.04 (s, 9H).

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. customto provide product (7.1 mg, 70% crude yield)

Sources & evidence

ORD record
ord-acd405ba1bff4d1e910c276d24ea562b
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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