4-Methoxy-2-(trifluoromethyl)phenylboronic acid → (7bR,11aS)-6-[4-methoxy-2-(trifluoromethyl)phenyl]-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole

HRID 47542Notes

Reaction equation

HRID 47542 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[C:5]([C:12]([F:15])([F:14])[F:13])[CH:4]=1.Br[C:17]1[CH:18]=[C:19]2[C:23]3=[C:24]([CH2:26][S:27][CH2:28][CH2:29][N:22]3[C@H:21]3[CH2:30][CH2:31][N:32](C(OC(C)(C)C)=O)[CH2:33][C@@H:20]23)[CH:25]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:17]2[CH:18]=[C:19]3[C:23]4=[C:24]([CH2:26][S:27][CH2:28][CH2:29][N:22]4[C@H:21]4[CH2:30][CH2:31][NH:32][CH2:33][C@@H:20]34)[CH:25]=2)=[C:5]([C:12]([F:15])([F:14])[F:13])[CH:4]=1

Participants

3

Reactant 2

HCID 121094604-Methoxy-2-(trifluoromethyl)phenylboronic acidHCID 86586435tert-butyl (7bR,11aS)-6-bromo-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H)-carboxylate

Product 1

HCID 60071881(7bR,11aS)-6-[4-methoxy-2-(trifluoromethyl)phenyl]-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole

Procedure

Using 4-methoxy-2-(trifluoromethyl)phenyl boronic acid and following the procedures described in EXAMPLE 9, tert-butyl (7bR,11aS)-6-bromo-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H)-carboxylate was converted into the title compound of EXAMPLE 12. 1H NMR(CDCl3, 300 MHz): δ 7.20 (m, 3H), 7.05 (m, 2H), 6.89 (s, 1H), 6.79 (s, 1H), 3.84 (s, 3H), 3.81 (m, 2H), 3.59 (m, 1H), 3.45 (m, 1H), 3.21 (m, 2H), 3.0 (m, 2H), 2.92 (m, 3H), 2.60 (m, 1H), 1.80 (m, 2H). LRMS (ES+): 421 (M+H)+.

Sources & evidence

ORD record
ord-7e07ce4bf2054935a30b93c06ef61da5
Source dataset
uspto-grants-2004_03
Patent number
US06699852B2

Reaction notes

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