Methyl iodide → HCID 57421256, compound

HRID 333811Notes

Reaction equation

HRID 333811 reaction equation
COC(=O)CC1C=CC(Cl)=CC=1Cl.C(OC1C=C(C=CN=1)C(O)=O)C1C=CC=CC=1.C([O:38][C:39]1[CH:44]=[C:43]([C:45]([OH:60])([CH:50]([C:52]2[CH:57]=[CH:56][C:55]([Cl:58])=[CH:54][C:53]=2[Cl:59])[CH3:51])[C:46]([F:49])([F:48])[F:47])[CH:42]=[CH:41][N:40]=1)C1C=CC=CC=1.CI>[Pd]>[Cl:59][C:53]1[CH:54]=[C:55]([Cl:58])[CH:56]=[CH:57][C:52]=1[CH:50]([CH3:51])[C:45]([C:43]1[CH:42]=[CH:41][NH:40][C:39](=[O:38])[CH:44]=1)([OH:60])[C:46]([F:49])([F:48])[F:47]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 2734106Methyl 2,4-dichlorobenzeneacetateHCID 229262722-(Benzyloxy)pyridine-4-carboxylic acidHCID 252538282-(2-Benzyloxy-pyridin-4-yl)-3-(2,4-dichloro-phenyl)-1,1,1-trifluoro-butan-2-ol

Product 1

HCID 57421256HCID 57421256, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title compound was prepared in analogy to Example 1, steps 2 to 5, from 2,4-dichlorobenzeneacetic acid methyl ester [CAS Reg. No. 91361-41-0] and 2-benzyloxy-isonicotinic acid (which was made as described below from 2-chloro isonicotinic acid), leading to 2-(2-benzyloxy-pyridin-4-yl)-3-(2,4-dichloro-phenyl)-1,1,1-trifluoro-butan-2-ol, followed by cleavage of the benzyl protecting group by hydrogenation over Pd/C-10% (0.75 g) in ethyl actetate (150 ml). In step 4, methyl iodide was used as an alkylating agent and the improved procedure described in example 117 was used. MS (m/e)=364.0 [MH+].

Sources & evidence

ORD record
ord-d309e7615038445d9341d1f585083e9e
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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