Methyl 4-methoxyacetoacetate → HCID 86721449, compound

HRID 869598Notes

Reaction equation

HRID 869598 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].Br[CH2:12][C:13]1[CH:32]=[CH:31][C:16]2/[C:17](=[C:27](/[CH3:30])\[C:28]#[N:29])/[C:18]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:19]=3[O:20][CH2:21][C:15]=2[CH:14]=1>>[C:28](/[C:27](=[C:17]1/[C:18]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:19]=2[O:20][CH2:21][C:15]2[CH:14]=[C:13]([CH2:12][CH:5]([C:4](=[O:10])[CH2:3][O:2][CH3:1])[C:6]([O:8][CH3:9])=[O:7])[CH:32]=[CH:31][C:16]/1=2)/[CH3:30])#[N:29]

Participants

3

Reactant 2

HCID 123500Methyl 4-methoxyacetoacetateHCID 86721333(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile

Product 1

HCID 86721449HCID 86721449, compoundYield 83%

Procedure

[step 1] Using methyl 4-methoxy-3-oxobutanoate (816 mg, 5.58 mmol) and (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (1.0 g, 2.79 mmol) obtained in Reference Example 1, and in the same manner as in Reference Example 13G, step 1, (E)-methyl 2-{[11-(1-cyanoethylidene)-3-fluoro-6,11-dihydrodibenzo[b,e]oxepin-8-yl]methyl}-4-methoxy-3-oxobutanoate (977 mg, 83%) was obtained.

Workup

  1. customobtained in Reference Example 1

Sources & evidence

ORD record
ord-299d8aa6c820458c886f65c1e336b615
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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