(2,4-Dichlorophenyl)boronic acid → HCID 11581073, compound

HRID 1435934Notes

Reaction equation

HRID 1435934 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:13]1[CH:22]=[C:21]([O:23][CH3:24])[C:20]2[NH:19][CH2:18][C@@H:17]3[CH2:25][N:26](C(OC(C)(C)C)=O)[CH2:27][C@@H:16]3[C:15]=2[CH:14]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:22]=[C:21]([O:23][CH3:24])[C:20]2[NH:19][CH2:18][C@@H:17]3[CH2:25][NH:26][CH2:27][C@@H:16]3[C:15]=2[CH:14]=1

Participants

3

Reactant 2

HCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 68971616HCID 68971616, compound

Product 1

HCID 11581073HCID 11581073, compound

Procedure

Following the procedures described in Example 12, except that 2,4-dichlorophenylboronic 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 15. 1H NMR (CDCl3): δ 7.48 (s, 1H), 7.34-7.25 (m, 2H), 6.76 (s, 1H), 6.74 (s, 1H), 4.55 (broad s, 1H), 3.87 (s, 3H), 3.65-3.57 (m, 1H), 3.50-3.25 (overlapping m, 4H), 3.13-2.97 (m, 2H), 2.75-2.65 (m, 1H). LRMS (ES)+: 349.3/351.3 (M+H)+.

Sources & evidence

ORD record
ord-164dc9a1914f4e4b8773bf5715e6f5ae
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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