3,4-Dichlorobenzeneboronic acid → HCID 86594675, compound

HRID 1292879Notes

Reaction equation

HRID 1292879 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([C@H:12]4[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][CH2:14][C@H:13]4[N:8]3[CH2:7][CH2:6][CH2:5]2)[CH:11]=1.[Cl:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][C:31]=1[Cl:32]>>[Cl:25][C:26]1[CH:27]=[C:28]([C:2]2[CH:3]=[C:4]3[C:9]4=[C:10]([C@H:12]5[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:15][CH2:14][C@H:13]5[N:8]4[CH2:7][CH2:6][CH2:5]3)[CH:11]=2)[CH:29]=[CH:30][C:31]=1[Cl:32]

Participants

3

Reactant 2

HCID 27343303,4-Dichlorobenzeneboronic acidHCID 10157379HCID 10157379, compound

Product 1

HCID 86594675HCID 86594675, compound

Procedure

The title compound was prepared by the method of Example 109 from tert-butyl (±)-cis-2-bromo-5,6,8,9,11,11a-hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-carboxylate (101.7 mg, 0.26 mmol) and 3,4-dichlorophenylboronic acid (97 mg, 0.52 mmol), after chromatographic purification (91.6 mg, 77%) as a white amorphous solid. 1H NMR (CDCl3, 300 MHz) δ 7.57 (d, 1H, J=1.8 Hz), 7.42 (d, 1H, J=8.4 Hz), 7.31 (dd, 1H, J=2.2, 8.4 Hz), 7.12 (bs, 1H), 7.07 (bs, 1H), 3.62-3.75 (m, 1H), 3.48-60 (m, 1H), 3.15-3.35 (m, 4H), 2.65-2.80 (m, 4H), 2.10-2.20 (m, 2H), 1.85-2.00 (m, 2H), 1.46 (s, 9H) ppm.

Workup

  1. customafter chromatographic purification (91.6 mg, 77%) as a white amorphous solid

Sources & evidence

ORD record
ord-8fa28aa376a146f4968e5cb83ac306dd
Source dataset
uspto-grants-2007_07
Patent number
US07238690B2

Reaction notes

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