(2,4-Dichlorophenyl)boronic acid → HCID 86591147, compound

HRID 1789971Notes

Reaction equation

HRID 1789971 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@@H:13]3[CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17][C@@H:12]3[N:6]3[CH2:7][CH2:8][NH:9][C:10]([CH:11]=1)=[C:5]23.[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1B(O)O>>[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[C:2]1[CH:3]=[C:4]2[C@@H:13]3[CH2:14][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:16][CH2:17][C@@H:12]3[N:6]3[CH2:7][CH2:8][NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

3

Reactant 2

HCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 86591148HCID 86591148, compound

Product 1

HCID 86591147HCID 86591147, compoundYield 61.8%

Procedure

Tert-butyl (6bR,10aS)-5-(2,4-dichlorophenyl)-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (37 mg, 60%) was prepared via coupling of tert-butyl (6bR,10aS)-5-bromo-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (50 mg, 0.13 mmol) with 2,4-dichlorophenyl boronic acid (74 mg, 0.39 mmol) as illustrated above using the general procedure for Suzuki coupling. 1H NMR (CDCl3, 300 MHz) δ 1.46 (s, 9H), 1.82–1.96 (m, 2H), 2.74–2.82 (m, 1H), 2.99–3.05 (m, 1H), 3.16–3.22 (m, 2H), 3.33–3.39 (m, 1H), 3.43–3.50 (m, 1H), 3.52–3.57 (m, 1H), 3.62–3.69 (m, 1H), 3.43–3.50 (m, 1H), 3.52–3.57 (m, 1H), 3.62–3.69 (m, 1H), 3.71–3.79 (m, 1H), 3.80–3.85 (m, 1H), 3.89–4.14 (m, 1H), 6.44 (s, 1H), 6.59 (s, 1H), 7.22 (s, 2H), 7.42 (s, 1H) ppm.

Sources & evidence

ORD record
ord-7284b827a7f341c185594aec89c7eb91
Source dataset
uspto-grants-2006_07
Patent number
US07071186B2

Reaction notes

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