Tetrahydrofuran → HCID 178518663, compound

HRID 1014705Notes

Reaction equation

Br[C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7](C(OC(C)(C)C)=O)=[N:8][C:4]=2[CH:3]=1.BrC1C=C[C:22]2[NH:23][CH:24]=[N:25][C:21]=2C=1.C(OC(OC(C)(C)C)=O)([O:30][C:31](C)(C)[CH3:32])=O.C(N(CC)CC)C.C[N:51]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][N:54]=1)[CH3:52].[O:59]1CCCC1>>[NH:6]1[C:5]2[CH:16]=[CH:17][C:2]([C:22]3[N:23]=[C:24]4[N:54]([CH2:55][CH:56]5[CH2:57][CH2:58][O:30][CH2:31][CH2:32]5)[C:53](=[O:59])[NH:51][C:52]4=[N:25][CH:21]=3)=[CH:3][C:4]=2[N:8]=[CH:7]1

Participants

Reactant 6

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 218852-Dimethylaminopyridine

HCID 90495Di-tert-butyl dicarbonate

HCID 178419331HCID 178419331, compound

HCID 178450787tert-Butyl 5-bromo-1H-benzo[d]imidazole-2-carboxylate

Product 1

HCID 178518663HCID 178518663, compoundYield 54%

Procedure

tert-Butyl 5-bromo-1H-benzo[d]imidazole-2-carboxylate. A solution of 5-bromo-1H-benzimidazole (1.06 g, 5.38 mmol), di-tert-butyl dicarbonate (1.3 g, 5.91 mmol), triethylamine (0.9 mL, 6.45 mmol) and dimethylaminopyridine (few crystals) in anhydrous tetrahydrofuran (15 mL) was allowed to stir at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the crude product was purified by Biotage chromatography (0-55% ethyl acetate in hexanes) to provide the desired product (0.85 g, 54%) as a white solid. MS (ESI) m/z 297.3 [M+1]+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe crude product was purified by Biotage chromatography (0-55% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-5965746d521e48448d808778af3131c2
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981893B2

Reaction notes

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