4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 4-(5-(2-(Dimethylamino)ethoxy)pyridin-2-yl)phenol

HRID 1518380Notes

Reaction equation

HRID 1518380 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:66]=[CH:65][C:64]([O:67][CH2:68][CH2:69][N:70]([CH3:72])[CH3:71])=[CH:63][CH:62]=1.CC1(C)C(C)(C)OB([C:81]2[CH:86]=[CH:85][C:84]([OH:87])=[CH:83][CH:82]=2)O1>>[CH3:71][N:70]([CH3:72])[CH2:69][CH2:68][O:67][C:64]1[CH:63]=[CH:62][C:61]([C:81]2[CH:86]=[CH:85][C:84]([OH:87])=[CH:83][CH:82]=2)=[N:66][CH:65]=1

Participants

5

Reactant 4

HCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 44340927{2-[(6-Chloropyridin-3-yl)oxy]ethyl}dimethylamineHCID 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 1360277234-(5-(2-(Dimethylamino)ethoxy)pyridin-2-yl)phenol

Procedure

Compound 90B was prepared in a similar manner to the synthesis of compound 34D by substituting compound 34C and 4-(hydroxymethyl)phenylboronic acid with compound 90A and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, respectively: 1H NMR (DMSO-d6): δ 9.56 (s, 1H), 8.29 (d, J=2.76 Hz, 1H), 7.83 (d, J=8.59 Hz, 2H), 7.74 (d, J=8.59 Hz, 2H), 7.41 (dd, J=8.59, 2.76 Hz, 2H), 6.82 (d, J=8.29 Hz, 2H), 4.14 (t, J=5.68 Hz, 2H), 2.64 (t, J=5.68 Hz, 2H), 2.22 (s, 6H). ESI (+)/MS: 258 (M+H)+.

Sources & evidence

ORD record
ord-3e0a28fd3aaf4d7d9998c177fa4ce892
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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