Sodium Carbonate → N-(7-(4-methoxyphenyl)benzo[d]thiazol-2-yl)acetamide

HRID 2077519Notes

Reaction equation

HRID 2077519 reaction equation
Br[C:2]1[C:10]2[S:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>CCO.COCCOC.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>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[C:10]3[S:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[N:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 57584914N-(7-bromobenzo[d]thiazol-2-yl)acetamide

Product 1

HCID 57585090N-(7-(4-methoxyphenyl)benzo[d]thiazol-2-yl)acetamide

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

N-(7-Bromobenzo[d]thiazol-2-yl)acetamide (56.5 mg, 0.208 mmol), 4-methoxybenzeneboronic acid (47.8 mg, 0.315 mmol), dichlorobis(triphenyl-phosphine)palladium (II) (30.7 mg, 43.7 μmol), and sodium carbonate (0.31 mL, 2 M, 0.62 mmol) were suspended in EtOH (0.25 mL) and 1,2-dimethoxyethane (0.9 mL). The flask was fit with a reflux condensor and placed in a preheated oil bath (85° C.) and stirred under nitrogen for 50 minutes. The reaction was cooled to RT, and filtered through a pad of Celite® (diatomaceous earth). This pad was washed with DCM and MeOH, and the filtrate was concentrated and filtered through a silica gel pad with 10:1 DCM/MeOH. The filtrate was concentrated and purified on HPLC (10-95% MeCN/water with 0.1% TFA over 30 minutes) to provide N-(7-(4-methoxyphenyl)benzo[d]thiazol-2-yl)acetamide. MS (ESI pos. ion) m/z: 299 (MH+). Calculated exact mass for C16H14N2O2S: 298. 1H NMR (400 MHz, DMSO-d6): 12.34 (s, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.63 (d, J=8.5 Hz, 5H), 7.51 (t, J=7.8 Hz, 1H), 7.34 (d, J=7.5 Hz, 1H), 7.12 (d, J=8.5 Hz, 2H), 3.81 (s, 3H), 2.20 (s, 3H).

Workup

  1. customplaced in a preheated oil bath
  2. temperatureThe reaction was cooled to RT
  3. filtrationfiltered through a pad of Celite® (diatomaceous earth)
  4. washThis pad was washed with DCM and MeOH
  5. concentrationthe filtrate was concentrated
  6. filtrationfiltered through a silica gel pad with 10:1 DCM/MeOH
  7. concentrationThe filtrate was concentrated
  8. custompurified on HPLC (10-95% MeCN/water with 0.1% TFA over 30 minutes)

Sources & evidence

ORD record
ord-83dbf141df294ccc859ac7050c47781d
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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