Phenylacetylene → HCID 10295930, compound

HRID 1297126Notes

Reaction equation

HRID 1297126 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[N:12]([CH2:23][CH3:24])[C:11](=[O:25])[CH2:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(OCC1C=CC=CC=1)C#C.[C:37]1([C:43]#[CH:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[CH2:23]([N:12]1[C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=2[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:44]#[C:43][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:3]=2)=[N:9][CH2:10][C:11]1=[O:25])[CH3:24]

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 6917484((Prop-2-yn-1-yloxy)methyl)benzeneHCID 10111768HCID 10111768, compound

Product 1

HCID 10295930HCID 10295930, compoundYield 33%

Procedure

By replacing 5-(4-bromophenyl)-1-ethyl-7,8-dimethoxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one (IIbl) in example IIbn by 5-(3-bromophenyl)-1-ethyl-7,8-dimethoxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one (IIbm), and [(prop-2-ynyloxy)methyl]benzene by phenylacetylene, and proceeding in the same manner, the abovenamed product is obtained. Yield: 33%. M: 100–102° C. 1H-NMR (CDCl3, 200 MHz): d 1.13 (s, 3H, CH3), 3.51–3.82 (m, 5H, 1H NCH2+1H CH2+OCH3), 3.97 (s, 3H, OCH3), 4.24–4.34 (m, 1H, NCH2), 4.74–4.80 (m, 1H, CH2), 6.66 (s, 1H Ar), 6.84 (s, 1H Ar), 7.26–7.83 (m, 9H Ar).

Workup

  1. customthe abovenamed product is obtained
  2. custom100–102° C

Sources & evidence

ORD record
ord-519d92b2539345819a36d250fa5e82eb
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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