Methyl 4-iodobenzoate → HCID 15956327, compound

HRID 724953Notes

Reaction equation

HRID 724953 reaction equation
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([C:14]#[CH:15])=[CH:13][C:8]=2[C:7](=[O:16])[N:6]([CH3:17])[C:5]2[CH:18]=[CH:19][CH:20]=[N:21][C:4]1=2)[CH3:2].I[C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1.N1C2C(=NC(=O)C3C=CC=NC=3N=2)C=CC=1>>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH2:14][CH2:15][C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=3)=[CH:13][C:8]=2[C:7](=[O:16])[N:6]([CH3:17])[C:5]2[CH:18]=[CH:19][CH:20]=[N:21][C:4]1=2)[CH3:2]

Participants

4

Reactant 3

HCID 69273Methyl 4-iodobenzoateHCID 10802535HCID 10802535, compoundHCID 23119574HCID 23119574, compound

Product 1

HCID 15956327HCID 15956327, compoundYield 14.7%

Procedure

5,11-dihydro-11-ethyl-8-ethynyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.1 g, 0.36 mmol) was coupled with methyl 4-iodobenzoate (0.1 g, 0.38 mmol) by a procedure analogous to that described in Example 51b to give 79 mg of an olefinic coupled product, 5,11-Dihydro-11-ethyl-5-methyl-8-[2-(4-methoxycarbonylphenyl)ethen-1-yl]-(-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one. Hydrogenation as described in Example 56 afforded 22 mg of the title compound, m.p. 172°-173° C. (ethyl acetate/hexanes).

Workup

  1. customto give 79 mg of

Sources & evidence

ORD record
ord-37ed028f3ee94b29977141abe18ad2f1
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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