5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one → (E)-5-(8-Fluoro-10,11-dihydro-benzo[4,5]cyclohepta[1,2-b]pyridin-5-ylidenemethyl)-1,3-dihydro-benzoimidazol-2-one

HRID 2218758Notes

Reaction equation

HRID 2218758 reaction equation
Br/[CH:2]=[C:3]1\[C:4]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:5]=2[CH2:6][CH2:7][C:8]2[C:13]\1=[CH:12][CH:11]=[CH:10][N:9]=2.CC1(C)C(C)(C)OB([C:27]2[CH:36]=[CH:35][C:30]3[NH:31][C:32](=[O:34])[NH:33][C:29]=3[CH:28]=2)O1>>[F:18][C:15]1[CH:16]=[CH:17][C:4]2/[C:3](=[CH:2]\[C:27]3[CH:36]=[CH:35][C:30]4[NH:31][C:32](=[O:34])[NH:33][C:29]=4[CH:28]=3)/[C:13]3[C:8]([CH2:7][CH2:6][C:5]=2[CH:14]=1)=[N:9][CH:10]=[CH:11][CH:12]=3

Participants

3

Reactant 2

HCID 438110655-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-oneHCID 59770460(E)-5-bromomethylene-8-fluoro-10,11-dihydro-benzo[4,5]cyclohepta[1,2-b]pyridine

Product 1

HCID 10473520(E)-5-(8-Fluoro-10,11-dihydro-benzo[4,5]cyclohepta[1,2-b]pyridin-5-ylidenemethyl)-1,3-dihydro-benzoimidazol-2-oneYield 60%

Procedure

Following procedures essentially as desctribed in Example 219, beginning with (E)-5-bromomethylene-8-fluoro-10,11-dihydro-benzo[4,5]cyclohepta[1,2-b]pyridine (100 mg, 0.33 mmol) and 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-benzoimidazol-2-one (111 mg, 0.43 mmol). After work-up, purify the crude product by flash chromatography (100% ethyl acetate to 10% ethanol/ethyl acetate) to provide 70 mg (60%) of purified product. LCMS (APCI-pos): 358.0 (M+H). LCMS (APCI-neg): 356.0 (M−H). Purity by LCMS (UV Area percent): 99%. 1HNMR (d6-DMSO, 400 MHz): δ10.56 (s, 1H), 10/46 (s, 1H), 8.38 (dd, 1H), 7.88 (dd, 1H), 7.28 (dd, 1H), 7.23 (dd, 1H), 6.96-6.90 (m, 2H), 6.89 (s, 1H), 6.73 (d, 1H), 6.68 (d, 1H), 6.52 (s, 1H), 3.5-3.3 (m, 2H), 3.1-2.9 (m, 2H).

Workup

  1. customAfter work-up, purify the crude product by flash chromatography (100% ethyl acetate to 10% ethanol/ethyl acetate)

Sources & evidence

ORD record
ord-fc90f2e0272741be957cffd724b19071
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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