4-Methyloxane-4-carbaldehyde → HCID 178506127, compound

HRID 1512181Notes

Reaction equation

HRID 1512181 reaction equation
[Br:1][C:2]12[CH2:9][CH2:8][C:5]([CH:10]=[CH:11][C:12](Cl)=O)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.COC(C12CCC(Br)(CC1)CC2)=O.CC1(C=O)CCOCC1.[N+:37]([C:40]1[CH:41]=[C:42]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[C:53]([F:56])([F:55])[F:54])[CH:43]=[CH:44][C:45]=1[NH2:46])([O-])=O>>[Br:1][C:2]12[CH2:9][CH2:8][C:5](/[CH:10]=[CH:11]/[C:12]3[NH:46][C:45]4[CH:44]=[CH:43][C:42]([C:47]5[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=5[C:53]([F:54])([F:55])[F:56])=[CH:41][C:40]=4[N:37]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2

Participants

5

Reactant 4

HCID 205923884-Methyloxane-4-carbaldehydeHCID 509940363-Nitro-2'-trifluoromethyl-biphenyl-4-ylamineHCID 57467434Methyl 4-bromobicyclo(2.2.2)octane-1-carboxylateHCID 866476843-(4-Bromo-bicyclo[2.2.2]oct-1-yl)-acryloyl chloride

Product 1

HCID 178506127HCID 178506127, compound

Procedure

(E)-2-[2-(4-Bromo-bicyclo[2.2.2]oct-1-yl)-vinyl]-5-(2-trifluoromethyl-phenyl)-1H-benzoimidazole was prepared from 3-(4-bromo-bicyclo[2.2.2]oct-1-yl)-acryloyl chloride (prepared from 4-bromo-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester utilizing a procedure analogues to the preparation of 4-methyl-tetrahydro-pyran-4-carbaldehyde in Example 9) and 3-nitro-2′-trifluoromethyl-biphenyl-4-ylamine (prepared as described in Example 3, STEP A) according to the procedure as described in Example 9, STEPS A-C.

Sources & evidence

ORD record
ord-37c4aa0b81be459982be3ed1e6f7510a
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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