4-Bromothiophene-3-carbonitrile → 4-(4-Hydroxyphenyl)thiophene-3-carbonitrile

HRID 1518328Notes

Reaction equation

HRID 1518328 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.Br[C:61]1[C:62]([C:66]#[N:67])=[CH:63][S:64][CH:65]=1.CC1(C)C(C)(C)OB([C:76]2[CH:81]=[CH:80][C:79]([OH:82])=[CH:78][CH:77]=2)O1>>[OH:82][C:79]1[CH:80]=[CH:81][C:76]([C:61]2[C:62]([C:66]#[N:67])=[CH:63][S:64][CH:65]=2)=[CH:77][CH:78]=1

Participants

5

Reactant 4

HCID 9013754-Bromothiophene-3-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 594475724-(4-Hydroxyphenyl)thiophene-3-carbonitrile

Procedure

Compound 51A was prepared in a similar manner to the synthesis of compound 34D by substituting compound 34C and 4-(hydroxymethyl)phenylboronic acid with 4-bromothiophene-3-carbonitrile and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, respectively: 1H NMR (DMSO-d6): δ 9.68 (s, 1H), 8.62 (d, J=3.38 Hz, 1H), 7.73 (d, J=3.07 Hz, 1H), 7.44 (d, J=8.59 Hz, 2H), 6.86 (d, J=8.59 Hz, 2H). MS (ESI(+)): m/z 200 (M−H).

Sources & evidence

ORD record
ord-1db2d793511a4e238ba57aec1e2439aa
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

Loading…