4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 59447539, compound

HRID 1518364Notes

Reaction equation

HRID 1518364 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:65]2[N:66]=[CH:67][N:68]=[C:69]([N:70]3[CH2:75][CH2:74][N:73]([CH3:76])[CH2:72][CH2:71]3)[C:64]=2[S:63][CH:62]=1.CC1(C)C(C)(C)OB([C:85]2[CH:90]=[CH:89][C:88]([OH:91])=[CH:87][CH:86]=2)O1>>[CH3:76][N:73]1[CH2:74][CH2:75][N:70]([C:69]2[C:64]3[S:63][CH:62]=[C:61]([C:85]4[CH:90]=[CH:89][C:88]([OH:91])=[CH:87][CH:86]=4)[C:65]=3[N:66]=[CH:67][N:68]=2)[CH2:71][CH2:72]1

Participants

5

Reactant 4

HCID 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-carboxylateHCID 59447618HCID 59447618, compound

Product 1

HCID 59447539HCID 59447539, compound

Procedure

The compound 79B was prepared in a similar manner to the synthesis of compound 34D by substituting compound 34C and 4-(hydroxymethyl)phenylboronic acid with compound 79A and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, respectively: 1H NMR (DMSO-d6): δ 9.56 (s, 1H), 8.63 (s, 1H), 8.28 (s, 1H), 7.85-7.89 (m, 2H), 6.48-6.88 (m, 2H), 4.06 (br, 4H), 2.91 (br, 4H), 2.53 (s, 3H). ESI (+)/MS: 327 (M+H)+.

Sources & evidence

ORD record
ord-5a1590426a0a4fc1a28a852c30d1e417
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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