tert-butyl 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-butyl 4-(2-(1-methyl-6-((perfluorophenoxy)sulfonyl)-1H-indol-3-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1524401Notes

Reaction equation

Br[C:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11]([O:14][C:15]3[C:20]([F:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:16]=3[F:25])(=[O:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH3:26])[CH:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:36]=2[C:45]2[CH2:50][CH2:49][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:47][CH:46]=2)O1>>[CH3:26][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([S:11]([O:14][C:15]3[C:20]([F:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:16]=3[F:25])(=[O:13])=[O:12])[CH:6]=2)[C:2]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:42])[F:43])=[CH:37][C:36]=2[C:45]2[CH2:50][CH2:49][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:47][CH:46]=2)=[CH:3]1

Participants

Reactant 2

HCID 71259448tert-butyl 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate2×

HCID 89407702perfluorophenyl 3-bromo-1-methyl-1H-indole-6-sulfonate

Product 1

HCID 89407773tert-butyl 4-(2-(1-methyl-6-((perfluorophenoxy)sulfonyl)-1H-indol-3-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

The title compound was prepared in an analogous manner to that described in Intermediate E using perfluorophenyl 3-bromo-1-methyl-1H-indole-6-sulfonate and tert-butyl 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (INTERMEDIATE N) as the coupling partners to afford tert-butyl 4-(2-(1-methyl-6-((perfluorophenoxy)sulfonyl)-1H-indol-3-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate as an orange oily solid. m/z (ESI) 726.3 (M+Na)+. 1H NMR (400 MHz, DMSO-d6) δ ppm=8.26 (d, J=1.5 Hz, 1 H), 7.95 (s, 1 H), 7.77-7.73 (m, 1 H), 7.72 (d, J=8.5 Hz, 1 H), 7.66 (d, J=8.0 Hz, 1 H), 7.63 (d, J=1.9 Hz, 1 H), 7.59 (dd, J=1.8, 8.6 Hz, 1 H), 5.82 (br. s., 1 H), 3.99 (s, 3 H), 3.84 (br. s., 2 H), 3.10 (t, J=5.5 Hz, 2 H), 1.89 (br. s., 2 H), 1.38-1.29 (m, 9 H).

Workup

customThe title compound was prepared in an analogous manner to that

Sources & evidence

ORD record: ord-21a0a78ebeab480aa520d487310007c5
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079902B2

Reaction notes

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