2-Chloronicotinonitrile → 2-(4-Hydroxyphenyl)nicotinonitrile

HRID 1518336Notes

Reaction equation

HRID 1518336 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[N:68]=[CH:67][CH:66]=[CH:65][C:62]=1[C:63]#[N:64].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[N:68]=[CH:67][CH:66]=[CH:65][C:62]=2[C:63]#[N:64])=[CH:78][CH:79]=1

Participants

5

Reactant 4

HCID 810792-ChloronicotinonitrileHCID 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 1360277242-(4-Hydroxyphenyl)nicotinonitrile

Procedure

Compound 56A was prepared in a similar manner to the synthesis of compound 34D by substituting compound 34C and 4-(hydroxymethyl)phenylboronic acid with 2-chloronicotinonitrile and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, respectively: ESI (+)/LC/MS: 197 (M+H)+.

Sources & evidence

ORD record
ord-173c808aa9e44e869242c47fec9f9c66
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

Loading…