Sodium Carbonate → 1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-4-yl)phenoxy)propan-2-ol

HRID 1399890Notes

Reaction equation

Br[C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][N:20]1[CH2:29][CH:30]([OH:48])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][N:20]1[CH2:29][CH:30]([OH:48])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:2]2[C:10]3[N:9]=[CH:8][N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole (200 mg, 0.611 mmol), 1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propan-2-ol (375 mg, 0.916 mmol), Pd(dppf)Cl2 (89 mg, 0.12 mmol) and Na2CO3 (130 mg, 1.22 mmol) in dioxane and H2O was stirred under N2 atmosphere at 100° C. for 3 h. The mixture was extracted with DCM and the combined organic layers dried over Na2SO4 and concentrated in vacuum to give the crude product (265 mg, Yield 82%) which was used without further purification.

Workup

extractionThe mixture was extracted with DCM
dry with materialthe combined organic layers dried over Na2SO4
concentrationconcentrated in vacuum

Sources & evidence

ORD record: ord-cf1550b8bb2742659a48d245f3f3b856
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906900B2

Reaction notes

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