Vinylpyrazine → HCID 86651976, compound

HRID 1615316Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:3]=1.[CH:21]([C:23]1[CH:28]=[N:27][CH:26]=[CH:25][N:24]=1)=[CH2:22].C(N(C(C)C)C(C)C)C>CC#N.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:24]1[CH:25]=[CH:26][N:27]=[CH:28][C:23]=1/[CH:21]=[CH:22]/[C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A degassed mixture of 3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (70 mg, 0.17 mmol), 2-vinylpyrazine (27 mg, 0.25 mmol), N-ethyl-N-isopropylpropan-2-amine (DIPEA, 45 mg, 0.35 mmol), Pd(OAc)2 (3.9 mg, 0.017 mmol) and P(o-MeC6H4)3 (16 mg, 0.052 mmol) in anh MeCN (2.5 mL) was heated with stirring in a sealed tube under microwave irradiation at 120° C. for 40 min. The crude mixture was later concentrated under reduced pressure and purified by prepTLC (SiO2 2:1 hexanes/EtOAc) to provide the title compound as a colorless solid (28 mg, 43%): 1H NMR (400 MHz, CDCl3) δ ppm 10.18 (s, 1H), 8.73 (s, 1H), 8.60 (br. s., 1H), 8.47 (d, J=2.26 Hz, 1H), 8.14-8.18 (m, 2H), 8.07 (d, J=16.06 Hz, 1H), 7.84 (d, J=8.53 Hz, 1H), 7.61 (d, J=16.31 Hz, 1H), 5.85 (s, 2H), 3.61 (t, J=8.28 Hz, 2H), 0.94 (t, J=8.53 Hz, 2H), −0.05 (s, 9H); MS ESI 381.2 [M+H]+, calcd for [C20H24N4O2Si+H]+ 381.5.

Workup

temperaturewas heated
concentrationThe crude mixture was later concentrated under reduced pressure
custompurified by prepTLC (SiO2 2:1 hexanes/EtOAc)

Sources & evidence

ORD record: ord-f2dc53aeed90413aac773417508b730b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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