HCID 89501111, compound → HCID 89501252, compound

HRID 64152Notes

Reaction equation

Br[C:2]1[CH:27]=[CH:26][C:5]2[N:6]([C:9]3[CH:10]=[C:11]([NH:22][C:23](=[O:25])[CH3:24])[CH:12]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=4)[CH:14]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1.[CH3:28][C:29]([OH:47])([CH2:31][CH2:32][N:33]1[CH:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[N:34]1)[CH3:30]>>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[CH:14]=[C:9]([N:6]3[C:5]4[CH:26]=[CH:27][C:2]([C:36]5[CH:35]=[N:34][N:33]([CH2:32][CH2:31][C:29]([OH:47])([CH3:28])[CH3:30])[CH:37]=5)=[CH:3][C:4]=4[N:8]=[CH:7]3)[CH:10]=[C:11]([NH:22][C:23](=[O:25])[CH3:24])[CH:12]=2)=[CH:16][CH:17]=1

Participants

Reactant 2

HCID 89501111HCID 89501111, compound

HCID 89501134HCID 89501134, compound

Product 1

HCID 89501252HCID 89501252, compoundYield 22.2%

Procedure

The compound was prepared from N-(5-(5-bromo-1H-benzo[d]imidazol-1-yl)-4′-fluoro-[1,1′-biphenyl]-3-yl)acetamide (0.07 g, 0.164 mmol) using the procedure of Example 200(c) and 2-methyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)butan-2-ol (0.092 g, 0.329 mmol, 2.0 eq.) to give the title product in 22.2% yield (0.018 g). 1H NMR (300 MHz, DMSO-d6): δ 10.42 (s, 1H), 8.68 (s, 1H), 8.25 (s, 1H), 7.99 (d, 2H), 7.93 (s, 1H), 7.83 (s, 1H), 7.69 (m, 2H), 7.65 (m, 1H), 7.61 (m, 2H), 7.36 (t, 2H), 4.48 (s, 1H); 4.26 (m, 2H); 2.12 (s, 3H); 1.91 (m, 2H); 1.15 (s, 6H); LC-MS (ESI): Calculated mass: 497.56 Observed mass: 497.9 [M+H]+ (rt: 0.9 min).

Sources & evidence

ORD record: ord-739135b4faff4c6295aed07313e8f30d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447091B2

Reaction notes

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