Methyl 2-bromopropionate → HCID 140590449, compound

HRID 1404859Notes

Reaction equation

HRID 1404859 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:10][C:11]([NH:13]/[N:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:26]=[CH:25][N:24]([C:27]4[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=4)[N:23]=3)=[CH:18][CH:17]=2)=[S:12])[CH2:3][CH2:2]1.C([O-])(=O)C.[Na+].Br[CH:44]([CH3:49])[C:45](OC)=[O:46]>CCO.C(Cl)Cl>[CH:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:10]2[C:45](=[O:46])[CH:44]([CH3:49])[S:12]/[C:11]/2=[N:13]/[N:14]=[CH:15]\[C:16]2[CH:17]=[CH:18][C:19]([C:22]3[N:26]=[CH:25][N:24]([C:27]4[CH:28]=[CH:29][C:30]([O:33][C:34]([F:35])([F:37])[F:36])=[CH:31][CH:32]=4)[N:23]=3)=[CH:20][CH:21]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 95576Methyl 2-bromopropionateHCID 517045Sodium AcetateHCID 88851450HCID 88851450, compound

Product 1

HCID 140590449HCID 140590449, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To (E)-N-(2-cyclopropylphenyl)-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylidene)hydrazinecarbothioamide (100 mg, 0.191 mmol) and sodium acetate (63.0 mg, 0.765 mmol) in EtOH (4 mL) was added methyl 2-bromopropanoate (0.026 mL, 0.230 mmol). The reaction was heated to 60° C. overnight. The reaction was then heated to 85° C. for 72 hours. The reaction mixture was diluted with DCM and washed with water. The aqueous layer was extracted with DCM. The organic layers were poured through a phase separator and concentrated. Purification by flash column chromatography provided the title compound as a white solid (32.5 mg, 0.056 mmol, 30%): mp 112-115° C.; 1H NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 8.32 (s, 1H), 8.22 (d, J=8.3 Hz, 2H), 7.87-7.75 (m, 4H), 7.43-7.32 (m, 4H), 7.26-7.24 (m, 2H), 4.23 (q, J=7.3 Hz, 1H), 1.85-1.78 (m, 4H), 0.90-0.78 (m, 2H), 0.78-0.69 (m, 1H), 0.65-0.55 (m, 1H); ESIMS m/z 578 (M+H).

Workup

  1. temperatureThe reaction was then heated to 85° C. for 72 hours
  2. washwashed with water
  3. extractionThe aqueous layer was extracted with DCM
  4. additionThe organic layers were poured through a phase separator
  5. concentrationconcentrated
  6. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-858cd1bb9df840cd84399d830e91e5c0
Source dataset
uspto-grants-2014_12
Patent number
US08916183B2

Reaction notes

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