2-(Trifluoromethyl)benzeneboronic acid → HCID 11551992, compound

HRID 1435932Notes

Reaction equation

HRID 1435932 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.Br[C:15]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]2[NH:21][CH2:20][C@@H:19]3[CH2:27][N:28](C(OC(C)(C)C)=O)[CH2:29][C@@H:18]3[C:17]=2[CH:16]=1>>[CH3:26][O:25][C:23]1[C:22]2[NH:21][CH2:20][C@@H:19]3[CH2:27][NH:28][CH2:29][C@@H:18]3[C:17]=2[CH:16]=[C:15]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:13])([F:12])[F:1])[CH:24]=1

Participants

3

Reactant 2

HCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 68971616HCID 68971616, compound

Product 1

HCID 11551992HCID 11551992, compound

Procedure

Following the procedures described in Example 12, except that 2-(trifluoromethyl)phenylboronic acid was used instead of phenylboronic acid, (±)-cis-tert-butyl 8-bromo-6-methoxy-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]quinoline-2(9bH)-carboxylate from Example 11, Part A was converted into the title compound of Example 13. 1H NMR (CDCl3): δ 7.73 (d, 1H, J=7.7 Hz), 7.57-7.52 (m, 1H), 7.46-7.40 (m, 1H), 7.36 (d, 1H, J=7.4 Hz), 6.68 (s, 1H), 6.66 (s, 1H), 4.51 (broad s, 1H), 3.85 (s, 3H), 3.65-3.30 (overlapping m, 5H), 3.15-2.98 (m, 2H), 2.78-2.68 (m, 1H). LRMS (ES)+: 349.3 (M+H)+.

Sources & evidence

ORD record
ord-c29a40325ac546739256ad4574cdf622
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

Loading…