Ethyl Acetate → HCID 86700230, compound

HRID 879425Notes

Reaction equation

HRID 879425 reaction equation
Br[C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([CH3:29])=[CH:7][C:5]=2[N:6]=1.[CH3:30][NH:31][C:32]1[CH:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][C:33]=1[N+:47]([O-:49])=[O:48].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:25]([O:24][C@@H:18]([C:9]1[C:8]([CH3:29])=[CH:7][C:5]2[N:6]=[C:2]([C:35]3[CH:36]=[CH:37][C:32]([NH:31][CH3:30])=[C:33]([N+:47]([O-:49])=[O:48])[CH:34]=3)[S:3][C:4]=2[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH3:28])([CH3:27])[CH3:26]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 46739449N-Methyl-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Product 1

HCID 86700230HCID 86700230, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (497 mg, 1.00 mmol) in 1,4-dioxane (6 mL) was added N-methyl-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (417 mg, 1.50 mmol), Pd(PPh3)4 (58 mg, 0.05 mmol) and potassium carbonate solution (2 M aqueous, 1.5 mL, 3.0 mmol). The reaction mixture was stirred at 105° C. for 3 h and was then cooled to rt. EtOAc and H2O were added. The layers were separated, and the organic layer was dried, filtered, and concentrated in vacuo. The crude mixture was purified by CombiFlash (EtOAc/Hex) to give (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(4-(methylamino)-3-nitrophenyl)benzo[d]thiazol-6-yl)acetate. 1H NMR (400 MHz, CD3OD):δ 8.71 (s, 1H), 8.40 (m, 1H), 8.05 (dd, J=8.8, 2.4 Hz, 1H), 7.73 (s, 1H), 7.51-7.58 (m, 4H), 7.06 (d, J=8.8 Hz, 1H), 5.22 (s, 1H), 4.22 (m, 2H), 3.05 (d, J=4.8 Hz, 3H), 2.55 (s, 3H), 1.22 (t, J=7 Hz, 3H), 0.97 (s, 9H).

Workup

  1. temperaturewas then cooled to rt
  2. customThe layers were separated
  3. customthe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was purified by CombiFlash (EtOAc/Hex)

Sources & evidence

ORD record
ord-4a32ca58a96a41b08f2ce10e9eae5ae6
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

Loading…