2-(Benzyloxy)pyridine-4-carboxylic acid → 2-(2-Benzyloxy-pyridin-4-yl)-3-(2,4-dichloro-phenyl)-1,1,1-trifluoro-butan-2-ol

HRID 1097868Notes

Reaction equation

HRID 1097868 reaction equation
COC(=O)CC1C=CC([C:11]([F:14])([F:13])[F:12])=CC=1Cl.C1(COC2C=C(C(O)=O)C=CN=2)C=CC=CC=1.[CH2:34]([O:41][C:42]1[CH:47]=[C:46]([C:48](=[O:59])[CH:49]([C:51]2[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][C:52]=2[Cl:58])[CH3:50])[CH:45]=[CH:44][N:43]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>N1C=CC=CC=1>[CH2:34]([O:41][C:42]1[CH:47]=[C:46]([C:48]([OH:59])([CH:49]([C:51]2[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][C:52]=2[Cl:58])[CH3:50])[C:11]([F:14])([F:13])[F:12])[CH:45]=[CH:44][N:43]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 229262722-(Benzyloxy)pyridine-4-carboxylic acidHCID 574740532-Chloro-4-(trifluoromethyl)-benzeneacetic acid methyl esterHCID 668132461-(2-Benzyloxy-pyridin-4-yl)-2-(2,4-dichloro-phenyl)-propan-1-one

Product 1

HCID 252538282-(2-Benzyloxy-pyridin-4-yl)-3-(2,4-dichloro-phenyl)-1,1,1-trifluoro-butan-2-ol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title compound was prepared in analogy to the reaction sequence outlined in Example 1, steps 2 to 5, from 2-chloro-4-(trifluoromethyl)-benzeneacetic acid methyl ester and 2-(phenylmethoxy)-4-pyridinecarboxylic acid with the following modification: In the methylation step (Example 1, step 4), an inseparable mixture of the desired intermediate 1-(2-benzyloxy-pyridin-4-yl)-2-(2,4-dichloro-phenyl)-propan-1-one with the dimethylated compound 2-benzyloxy-4-[(E or Z)-2-(2,4-dichloro-phenyl)-1-methoxy-propenyl]-pyridine was obtained. This mixture was treated as follows:

Workup

  1. customwas obtained
  2. additionThis mixture was treated

Sources & evidence

ORD record
ord-6fe96ef319544dbe9d2a2c5d67605954
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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