3-Chloropyrazine-2-carbonitrile → 3-(4-Hydroxyphenyl)pyrazine-2-carbonitrile

HRID 1518370Notes

Reaction equation

HRID 1518370 reaction equation
S1C2C=CC=CC=2N=C1N(COCC[Si](C)(C)C)C(C1C=CC=C2C=1CN(C1SC(C3C=CC(CO)=CC=3)=C(C(OCC)=O)N=1)CC2)=O.OCC1C=CC(B(O)O)=CC=1.Cl[C:61]1[C:62]([C:67]#[N:68])=[N:63][CH:64]=[CH:65][N:66]=1.CC1(C)C(C)(C)OB([C:77]2[CH:82]=[CH:81][C:80]([OH:83])=[CH:79][CH:78]=2)O1>>[OH:83][C:80]1[CH:81]=[CH:82][C:77]([C:61]2[C:62]([C:67]#[N:68])=[N:63][CH:64]=[CH:65][N:66]=2)=[CH:78][CH:79]=1

Participants

5

Reactant 4

HCID 2924653-Chloropyrazine-2-carbonitrileHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 59447480ethyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(4-(hydroxymethyl)phenyl)thiazole-4-carboxylate

Product 1

HCID 1363371953-(4-Hydroxyphenyl)pyrazine-2-carbonitrile

Procedure

Compound 86A was prepared in a similar manner to the synthesis of compound 34D by substituting compound 34C and 4-(hydroxymethyl)phenylboronic acid with 3-chloropyrazine-2-carbonitrile and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, respectively: 1H NMR (DMSO-d6): δ 10.14 (s, 1H), 8.95 (d, J=2.45 Hz, 1H), 8.73 (d, J=2.45 Hz, 1H), 7.83-7.85 (m, 2H), 6.95-6.99 (m, 2H). ESI (+)/MS: 211 (M+H)+.

Sources & evidence

ORD record
ord-677b234b167b465a80f61391cda195c6
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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