3-Bromobenzonitrile → HCID 131732907, compound

HRID 2167512Notes

Reaction equation

HRID 2167512 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[C:10]([C@@H:13]([C@H:15]([C:17]([O-:19])=[O:18])[OH:16])[OH:14])([O-:12])=[O:11]>CO>[C:10]([C@@H:13]([C@H:15]([C:17]([OH:19])=[O:18])[OH:16])[OH:14])([OH:12])=[O:11].[C:5](#[N:6])[C:4]1[CH:7]=[CH:8][CH:9]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 233813-BromobenzonitrileHCID 119400Tartrate

Product 1

HCID 131732907HCID 131732907, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A procedure similar to Step C of Example 14 was used to couple 5-(4-chlorophenyl)-2,5-ethano-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1H-2-benzoazepine from Step B of Example 14 with 3-bromobenzonitrile. The desired coupling product was obtained and converted to the corresponding L-tartrate salt as in step C, except no methanol was used, to provide 34544-chlorophenyl)-2,5-ethano-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)benzonitrile, L-tartrate salt (36 mg, 26%, AUC HPLC 97.8%) as an off-white solid: 1H NMR (CD3OD, 500 MHz) δ 7.98 (s, 1H), 7.93-7.91 (m, 1H), 7.70 (d, J=7.5 Hz, 1H), 7.63-7.60 (m, 2H), 7.46 (d, J=8.0 Hz, 2H), 7.41 (d, J=8.5 Hz, 1H), 7.35 (d, J=8.5 Hz, 2H), 6.49 (d, J=8.0 Hz, 1H), 4.87 (br s, 2H), 4.41 (s, 2.2H), 3.68-3.50 (m, 2H), 3.50-3.35 (m, 2H), 2.81-2.75 (m, 2H), 2.48-2.41 (m, 2H); ESI MS m/z 385 [M+H]+. Anal. Calcd. For C25H21ClN2.1.1C4H6O6.1.75H2O: C, 60.72; H, 5.39; N, 4.82. Found: C, 60.72; H, 5.22; N, 4.96.

Workup

  1. customThe desired coupling product was obtained

Sources & evidence

ORD record
ord-5587ac64defa4d45b40464a281b16255
Source dataset
uspto-grants-2015_06
Patent number
US09045468B2

Reaction notes

Loading…