(E)-Ethyl 3-[4-[[3,5-bis(trimethylsilyl)benzoyl]amino]-2,5-difluorophenyl]-2-butenoate → (E)-Ethyl 3-[4-[[3,5-bis(trimethylsilyl)benzoyl]amino]-2-fluorophenyl]-2-butenoate

HRID 2265099Notes

Reaction equation

HRID 2265099 reaction equation
NC1C=CC(/C(/C)=C/C(OCC)=O)=C(F)C=1.[CH3:17][Si:18]([CH3:49])([CH3:48])[C:19]1[CH:20]=[C:21]([CH:41]=[C:42]([Si:44]([CH3:47])([CH3:46])[CH3:45])[CH:43]=1)[C:22]([NH:24][C:25]1[C:30](F)=[CH:29][C:28](/[C:32](/[CH3:39])=[CH:33]/[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:27]([F:40])[CH:26]=1)=[O:23]>>[CH3:47][Si:44]([CH3:45])([CH3:46])[C:42]1[CH:41]=[C:21]([CH:20]=[C:19]([Si:18]([CH3:17])([CH3:48])[CH3:49])[CH:43]=1)[C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28](/[C:32](/[CH3:39])=[CH:33]/[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:27]([F:40])[CH:26]=1)=[O:23]

Participants

3

Reactant 2

HCID 86644279(E)-Ethyl 3-[4-[[3,5-bis(trimethylsilyl)benzoyl]amino]-2,5-difluorophenyl]-2-butenoateHCID 86644280(E)-Ethyl 3-(4-amino-2-fluorophenyl)-2-butenoate

Product 1

HCID 86644281(E)-Ethyl 3-[4-[[3,5-bis(trimethylsilyl)benzoyl]amino]-2-fluorophenyl]-2-butenoateYield 42%

Procedure

Using BTMB (1.0 g) and Compound 11a (1.01 g), Compound 11b (739 mg, 42%) was obtained as a light yellow solid in the same manner as Compound 10b was synthesized.

Sources & evidence

ORD record
ord-95f176e317d04ffdacb74ee4fc522eef
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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