HCID 67210347, compound → HCID 67211328, compound

HRID 452197Notes

Reaction equation

HRID 452197 reaction equation
Br[C:2]1[CH:22]=[CH:21][C:5]2/[C:6](=[C:15](/[CH2:18][CH2:19][CH3:20])\[C:16]#[N:17])/[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[O:9][CH2:10][C:4]=2[CH:3]=1.Br[C:24]1[CH:44]=[CH:43][C:27]2/[C:28](=[C:37](\[CH2:40][CH2:41][CH3:42])/[C:38]#[N:39])/[C:29]3[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=3[O:31][CH2:32][C:26]=2[CH:25]=1.BrC1C=CC2/C(=C3\C(CC#N)C\3)/C3C=CC=C[C:52]=3[O:53][CH2:54][C:48]=2[CH:47]=1.BrC1C=CC2/C(=C3/C(CC#N)C/3)/C3C=CC=CC=3[O:75]CC=2C=1>>[C:16](/[C:15](=[C:6]1/[C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[O:9][CH2:10][C:4]2[CH:3]=[C:2]([C:30]([O:31][CH2:32][CH2:26][CH3:25])=[O:53])[CH:22]=[CH:21][C:5]/1=2)/[CH2:18][CH2:19][CH3:20])#[N:17].[C:38](/[C:37](=[C:28]1\[C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[O:31][CH2:32][C:26]2[CH:25]=[C:24]([C:52]([O:53][CH2:54][CH2:48][CH3:47])=[O:75])[CH:44]=[CH:43][C:27]\1=2)/[CH2:40][CH2:41][CH3:42])#[N:39]

Participants

6

Reactant 4

HCID 67210347HCID 67210347, compoundHCID 67210349HCID 67210349, compoundHCID 67210459HCID 67210459, compoundHCID 67211686HCID 67211686, compound

Product 2

HCID 67210917HCID 67210917, compoundHCID 67211328HCID 67211328, compoundYield 54%

Procedure

[step 1] Using pentanenitrile (2.7 mL, 25.9 mol) instead of cyclopropylacetonitrile, and in the same manner as in Reference Example B9, step 1, (E)-2-(8-bromo-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)pentanenitrile and (Z)-2-(8-bromo-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)pentanenitrile (1.90 g, 51%) were obtained. [step 2] Using (E)-2-(8-bromo-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)pentanenitrile and (Z)-2-(8-bromo-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)pentanenitrile (1.9 g, 5.37 mmol) obtained in Reference Example B11, step 1, instead of (E)-2-(8-bromo-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)cyclopropylacetonitrile and (Z)-2-(8-bromo-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)cyclopropylacetonitrile, and in the same manner as in Reference Example B9, step 2, propyl(E)-11-(1-cyanobutylidene)-6,11-dihydrodibenzo[b,e]oxepine-8-carboxylate and propyl(Z)-11-(1-cyanobutylidene)-6,11-dihydrodibenzo[b,e]oxepine-8-carboxylate (1.05 g, 54%) were obtained. [step 3] Using propyl(E)-11-(1-cyanobutylidene)-6,11-dihydrodibenzo[b,e]oxepine-8-carboxylate and propyl(Z)-11-(1-cyanobutylidene)-6,11-dihydrodibenzo[b,e]oxepine-8-carboxylate (1.05 g, 2.91 mmol) instead of propyl(E)-11-(1-cyanocyclopropylmethylene)-6,11-dihydrodibenzo[b,e]oxepine-8-carboxylate and propyl(Z)-11-(1-cyanocyclopropylmethylene)-6,11-dihydrodibenzo[b,e]oxepine-8-carboxylate, and in the same manner as in Example B9, step 3, (E)-2-(8-hydroxymethyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)pentanenitrile (0.370 g, 41%) was obtained.

Sources & evidence

ORD record
ord-fed5bf733ed0420283f1b222bda2f8b9
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

Loading…