HCID 86673710, compound → HCID 71008569, compound

HRID 1025595Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[C:17]([CH:33]=[O:34])=[C:18]([N:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]([C:31]#[N:32])=[CH:23]3)[CH:19]=[CH:20][CH:21]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].BrC1C(C=[O:54])=C(N2C3C(=CC=CC=3)C(C#N)=C2)C=CC=1>>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[C:17]([CH2:33][OH:34])=[C:18]([N:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]([C:31]([NH2:32])=[O:54])=[CH:23]3)[CH:19]=[CH:20][CH:21]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 86673710HCID 86673710, compound

HCID 86673712HCID 86673712, compound

Product 1

HCID 71008569HCID 71008569, compoundYield 66%

Procedure

The preparation of 1-(3-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)-2-formylphenyl)-1H-indole-3-carbonitrile, via reaction of 1-(3-bromo-2-formylphenyl)-1H-indole-3-carbonitrile (222 mg, 40% pure, 0.27 mmol, synthesis described above in Example 18, step 1) with 6-tert-butylphthalzin-1(2H)-one (138 mg, 0.68 mmol) was carried out in a procedure analogous to that described in Example 18. Similar work up and purification provided desired product as a light yellow-white solid (82 mg, 66% yield). LC/MS calcd for C28H22N4O2 (m/e) 446.51, obsd 447.0 (M+H, ES+): 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.44 (s, 9H) 7.23-7.40 (m, 3H) 7.55 (dd, J=7.93, 1.13 Hz, 2H) 7.72-7.94 (m, 6H) 8.32 (s, 1H) 8.39 (d, J=8.31 Hz, 1H) 9.59 (s, 1H).

Workup

customSimilar work up and purification

Sources & evidence

ORD record: ord-6cd2b1c156b24f15ab9bfde9d1ce50ab
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729078B2

Reaction notes

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