4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 136027728, compound

HRID 1518348Notes

Reaction equation

HRID 1518348 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:60][C:61]1[C:65]2[N:66]=[CH:67][N:68]=[C:69](Cl)[C:64]=2[S:63][CH:62]=1.CC1(C)C(C)(C)OB([C:79]2[CH:84]=[CH:83][C:82]([OH:85])=[CH:81][CH:80]=2)O1>>[Br:60][C:61]1[C:65]2[N:66]=[CH:67][N:68]=[C:69]([C:79]3[CH:84]=[CH:83][C:82]([OH:85])=[CH:81][CH:80]=3)[C:64]=2[S:63][CH:62]=1

Participants

5

Reactant 4

HCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 166552667-Bromo-4-chlorothieno[3,2-d]pyrimidineHCID 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 136027728HCID 136027728, compound

Procedure

The title compound was prepared using similar conditions as described for the synthesis of compound 34D by substituting compound 34C and 4-(hydroxymethyl)phenylboronic acid with compound 65A and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, respectively: 1H NMR (DMSO-d6): δ 9.27 (s, 1H), 8.73 (s, 1H), 8.08-8.10 (m, 2H), 7.01-7.03 (m, 2H); ESI (−)/MS: 308 (M−H)−.

Sources & evidence

ORD record
ord-4b6c79717a744349baf710268262c0a9
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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