3-Fluorophenylboronic acid → HCID 23541930, compound

HRID 1292875Notes

Reaction equation

HRID 1292875 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.[F:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1>>[F:24][C:25]1[CH:30]=[C:29]([C:2]2[CH:3]=[C:4]3[C:8]4=[C:9]([CH2:11][CH2:12][N:7]4[C@@H:6]4[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]34)[CH:10]=2)[CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 27339863-Fluorophenylboronic acidHCID 23541998HCID 23541998, compound

Product 1

HCID 23541930HCID 23541930, compound

Procedure

The title compound was prepared by the method of Example 90 tert-butyl (±)-cis-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate (125 mg, 0.28 mmol) and corresponding 3-fluorophenylboronic acid (77 mg, 0.56 mmol), to afford after chromatographic purification the title compound (48 mg, 44%) as a white amorphous solid. 1H NMR (CDCl3, 300 MHz) δ 7.20-7.40 (m, 2H), 7.10-7.20 (m, 3H), 6.80-7.00 (m, 1H), 3.80-3.90 (m, 1H), 3.60-3.80 (m, 1H), 3.10-3.50 (m, 7H), 2.80-3.00 (m, 1H), 1.70-1.90 (m, 2H), 1.48 (s, 9H) ppm. MS (CI, NH3): 395 (base, M+H).

Workup

  1. customto afford
  2. customafter chromatographic purification the title compound (48 mg, 44%) as a white amorphous solid

Sources & evidence

ORD record
ord-944b737231024d7ab06ca11ebe0e41ff
Source dataset
uspto-grants-2007_07
Patent number
US07238690B2

Reaction notes

Loading…