Sodium Carbonate → HCID 57584965, compound

HRID 2077522Notes

Reaction equation

HRID 2077522 reaction equation
Br[C:2]1[C:7]2[NH:8][C:9](=[O:11])[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:20]2[CH:32]=[CH:31][C:23]3[N:24]=[C:25]([NH:27][C:28](=[O:30])[CH3:29])[S:26][C:22]=3[CH:21]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:11]=[C:9]1[NH:8][C:7]2[C:2]([C:20]3[CH:32]=[CH:31][C:23]4[N:24]=[C:25]([NH:27][C:28](=[O:30])[CH3:29])[S:26][C:22]=4[CH:21]=3)=[CH:3][CH:4]=[CH:5][C:6]=2[S:10]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 151420034-Bromo-1,3-benzothiazol-2(3H)-oneHCID 51354026n-(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide

Product 1

HCID 57584965HCID 57584965, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

4-Bromobenzo[d]thiazol-2(3H)-one (69.9 mg, 0.304 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (124.9 mg, 3.925 mmol), dichlorobis(triphenyl-phosphine)palladium (II) (39.7 mg, 56.6 μmol), and sodium carbonate (0.30 mL, 2.0 M in water, 0.60 mmol) were suspended in 1,2-dimethoxyethane (1.4 mL) and ethanol (0.39 mL). The reaction flask was fit with a reflux condensor and the solution was heated in a preheated oil bath (85° C.) and stirred under nitrogen for 7 hours, at which time the reaction was slowly allowed to cool to RT. After sitting at RT for 4 days, more PdCl2(PPh3)2 (37.3 mg) was added, and stirring was resumed at 85° C. for 4 hours. Then, the reaction was cooled to RT and filtered through a silica gel plug with 10:1 DCM/MeOH. The filtrate was concentrated and purified on HPLC (10-95% MeCN/water with 0.1% TFA over 40 minutes) to provide N-(6-(2-oxo-2,3-dihydrobenzo[d]thiazol-4-yl)benzo[d]thiazol-2-yl)acetamide. MS (ESI pos. ion) m/z: 342 (MH+). Calculated exact mass for C16H11N3O2S2: 341.

Workup

  1. temperatureto cool to RT
  2. waitAfter sitting at RT for 4 days
  3. stirringstirring
  4. waitwas resumed at 85° C. for 4 hours
  5. temperatureThen, the reaction was cooled to RT
  6. filtrationfiltered through a silica gel plug with 10:1 DCM/MeOH
  7. concentrationThe filtrate was concentrated
  8. custompurified on HPLC (10-95% MeCN/water with 0.1% TFA over 40 minutes)

Sources & evidence

ORD record
ord-6df502fc5be2483c93c96decd227e12d
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

Loading…