2,4-Dimethoxybenzeneboronic acid → HCID 23541923, compound

HRID 1292876Notes

Reaction equation

HRID 1292876 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8]3=[C:9]([CH2:11][CH2:12][N:7]3[C@@H:6]3[CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][C@H:5]23)[CH:10]=1.[CH3:24][O:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=1B(O)O>>[CH3:24][O:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=1[C:2]1[CH:3]=[C:4]2[C:8]3=[C:9]([CH2:11][CH2:12][N:7]3[C@@H:6]3[CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:16][C@H:5]23)[CH:10]=1

Participants

3

Reactant 2

HCID 27343412,4-Dimethoxybenzeneboronic acidHCID 23541998HCID 23541998, compound

Product 1

HCID 23541923HCID 23541923, compound

Procedure

The title compound was prepared by the method of Example 90 from tert-butyl (±)-cis-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (143 mg, 0.32 mmol) and corresponding 2,4-dimethoxyphenylboronic acid (115 mg, 0.63 mmol), to afford after chromatographic purification the title compound (92 mg, 66%) as a white amorphous solid. 1H NMR (CDCl3, 300 MHz) δ 7.15-7.18 (m, 1H), 7.08 (s, 1H), 7.04 (s, 1H), 6.40-6.60 (m, 2H), 3.75-4.00 (m, 7H), 3.60-3.70 (m, 1H), 3.00-3.50 (m, 7H), 2.70-2.90 (m, 1H), 1.70-1.90 (m, 2H), 1.48 (s, 9H) ppm. MS (CI, NH3): 437 (base, M+H).

Workup

  1. customto afford
  2. customafter chromatographic purification the title compound (92 mg, 66%) as a white amorphous solid

Sources & evidence

ORD record
ord-0c90833f02304da495f2eed15ce05041
Source dataset
uspto-grants-2007_07
Patent number
US07238690B2

Reaction notes

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