Methyl bromoacetate → HCID 67279598, compound

HRID 1694352Notes

Reaction equation

HRID 1694352 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][Si](C(C)C)(C(C)C)C(C)C)[C:14]=3[O:30][CH3:31])[N:10]([C:32]([C:34]3[C:39]([F:40])=[CH:38][C:37]([F:41])=[CH:36][C:35]=3[F:42])=[O:33])[N:9]=2)=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Br[CH2:62][C:63]([O:65][CH3:66])=[O:64]>>[CH3:66][O:65][C:63](=[O:64])[CH2:62][O:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH:11]2[N:10]([C:32](=[O:33])[C:34]3[C:35]([F:42])=[CH:36][C:37]([F:41])=[CH:38][C:39]=3[F:40])[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[S:12]2)[C:14]=1[O:30][CH3:31]

Participants

4

Reactant 3

HCID 60984Methyl bromoacetateHCID 2724141Tetrabutylammonium FluorideHCID 67279300HCID 67279300, compound

Product 1

HCID 67279598HCID 67279598, compound

Procedure

[5-(4-fluoro-phenyl)-2-(2-methoxy-3-triisopropylsilanyloxy-phenyl)-[1,3,4]thiadiazol-3-yl]-(2,4,6-trifluoro-phenyl)-methanone (3.31 mmol), prepared as described in example 4, is treated with tetrabutylammonium fluoride (1 M in THF) (4.97 mmol) at room temperature for 40 minutes. Methyl bromoacetate (4.97 mmol) is then added. After 12 hours, the reaction is complete as determined by LC/MS. Purification is accomplished by silica flash chromatography (25% EtOAc/hexane) to give {3-[5-(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-2-methoxy-phenoxy}-acetic acid methyl ester: 1H NMR (400 MHz, CDCl3) δ 7.52 (m, 3H), 7.04 (m, 3H), 6.95 (dd, J1=8.4 Hz, J2=1.6 Hz, 1H), 6.82 (dd, J1=8 Hz, J2=1.6 Hz), 6.76 (m, 2H), 4.7 (s, 2H), 4.1 (s, 3H); LC/MS (ES+): 505.1 (M+1)+.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-86b1a183eb9448178184de1ff9e0128a
Source dataset
uspto-grants-2012_04
Patent number
US08158662B2

Reaction notes

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