(4-Methoxy-2-methylphenyl)boronic acid → HCID 11544358, compound

HRID 1435933Notes

Reaction equation

HRID 1435933 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[C:5]([CH3:12])[CH:4]=1.Br[C:14]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]2[NH:20][CH2:19][C@@H:18]3[CH2:26][N:27](C(OC(C)(C)C)=O)[CH2:28][C@@H:17]3[C:16]=2[CH:15]=1>>[CH3:25][O:24][C:22]1[C:21]2[NH:20][CH2:19][C@@H:18]3[CH2:26][NH:27][CH2:28][C@@H:17]3[C:16]=2[CH:15]=[C:14]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH3:12])[CH:23]=1

Participants

3

Reactant 2

HCID 2773486(4-Methoxy-2-methylphenyl)boronic acidHCID 68971616HCID 68971616, compound

Product 1

HCID 11544358HCID 11544358, compound

Procedure

Following the procedures described in Example 12, except that 4-methoxy-2-methylphenylboronic 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 14. 1H NMR (CDCl3): δ 7.14 (d, 1H, J=8.1 Hz), 6.83-6.73 (m, 2H), 6.62 (s, 1H), 6.61 (s, 1H), 4.49 (broad s, 1H), 3.85 (s, 3H), 3.84 (s, 3H), 3.78-3.70 (m, 1H), 3.62-3.05 (overlapping m, 6H), 2.83-2.75 (m, 1H), 2.28 (s, 3H). LRMS (ES)+: 325.4 (M+H)+.

Sources & evidence

ORD record
ord-a880ad8959934fda9f4317782627b316
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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