2-Methylphenyl boronic acid → HCID 10453012, compound

HRID 1266080Notes

Reaction equation

HRID 1266080 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][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O>>[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=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 27332672-Methylphenyl boronic acidHCID 20577007Tert-butyl (6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate

Product 1

HCID 10453012HCID 10453012, compound

Procedure

The title compound was prepared by the method of Example 89 step C from tert-butyl (6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH) carboxylate (189 mg, 0.5 mmol) and 2-methylphenylboronic acid (136 mg, 1.0 mmol) to afford after chromatographic purification the title compound (90 mg, 46%). 1H NMR (CDCl3, 300 MHz) δ7.11-7.18 (m,4H), 6.82 (s, 1H), 6.77 (s, 1H), 3.86-4.30 (m, 2H), 3.58-3.64 (m, 1H), 2.76-3.42 (m, 7H), 2.20 (s, 3H), 1.70-1.85 (m, 2H), 1.40 (s, 9H) ppm. MS-ApCI: 391 [M+H+].

Workup

  1. customto afford
  2. customafter chromatographic purification the title compound (90 mg, 46%)

Sources & evidence

ORD record
ord-4c057e602aa9443a8ff06dcd6fc7df93
Source dataset
uspto-grants-2003_04
Patent number
US06548493B1

Reaction notes

Loading…