Propargyl bromide → 10-(prop-2-ynyl)dibenzo[b,f][1,4]oxazepin-11(10H)-one

HRID 718100Notes

Reaction equation

HRID 718100 reaction equation
[CH:1]1[C:6]2[C:7](=[O:16])[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH2:18][C:19]#[CH:20].ClC1C=CC2NC(=O)C3C=CC=CC=3NC=2C=1>>[CH2:20]([N:8]1[C:7](=[O:16])[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]1=2)[C:19]#[CH:18]

Participants

4

Reactant 3

HCID 7842Propargyl bromideHCID 72374O-(o-Aminophenoxy)benzoic acid lactamHCID 215392327-chloro-5H-dibenzo[b,e][1,4]diazepin-11(10H)-one

Product 1

HCID 5978344810-(prop-2-ynyl)dibenzo[b,f][1,4]oxazepin-11(10H)-one

Procedure

Using Procedure H-3 (Table 5) with dibenzo[b,f][1,4]oxazepin-11(10H)-one and 3-bromoprop-1-yne the title compound 85 was obtained (1.58 g, 89%) as an off-white solid. 1H NMR (DMSO-d6) δ (ppm): 7.76 (ddd, J=7.5, 1.7, 0.4 Hz, 1H), 7.65 (dd, J=8.0, 1.7 Hz, 1H), 7.61 (ddd, J=8.2, 7.2, 1.8 Hz, 1H), 7.41 (dd, J=7.8, 1.6 Hz, 1H), 7.37 (ddd, J=8.2, 1.0, 0.4 Hz, 1H), 7.34-7.24 (m, 3H), 4.83 (d, J=2.3 Hz, 2H), 3.31 (t, J=2.3 Hz, 1H). MS (m/z): 250.0 (M+H)

Workup

  1. customwas obtained (1.58 g, 89%) as an off-white solid

Sources & evidence

ORD record
ord-f5ea69a7086b43228a74abd3165720dc
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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