Toluene → HCID 59385244, compound

HRID 2356799Notes

Reaction equation

HRID 2356799 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:11]3[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=3[N:13]=2)=[C:4]([F:19])[CH:3]=1.[C:20]([O-:23])([O-])=[O:21].[Na+].[Na+].ClCCl.O1CCOC[CH2:30]1.[C:35]1(C)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O>[F:19][C:4]1[CH:3]=[C:2]([C:35]2[CH:40]=[CH:39][C:38]([C:20]([O:23][CH3:30])=[O:21])=[CH:37][CH:36]=2)[CH:7]=[CH:6][C:5]=1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 7147089N-(4-bromo-2-fluorophenyl)-6-fluoro-1,3-benzothiazol-2-amine

Product 1

HCID 59385244HCID 59385244, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

As shown in Reaction Scheme 5, to a mixture of N-(4-bromo-2-fluorophenyl)-6-fluoro-1,3-benzothiazol-2-amine (1.00 g, 2.93 mmol) and 4-(methoxycarbonylphenyl)boronic acid (0.79 g, 4.40 mmol) in toluene (10 mL) was added Na2CO3 (1.40 g, 13.2 mmol), 1,1′-bis(diphenylphosphino) ferrocenepalladium(II) chloride complex with dichloromethane (0.05 g, 0.06 mmol), 1,4-dioxane (5 mL), and water (5 mL). This mixture was heated at reflux overnight. Upon cooling to rt, the reaction mixture was filtered, and the solid was washed with water (2×30 mL) and methanol (2×30 mL). The solid was recrystallized from acetone/MeOH (2:1). This yielded 0.641 g (55%) of the desired product as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 3.82 (s, 3H), 7.20 (t, 1H), 7.59-8.02 (m, 8H), 8.70 (t, 1H), 10.50 (bs, 1H).

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux overnight
  3. filtrationthe reaction mixture was filtered
  4. washthe solid was washed with water (2×30 mL) and methanol (2×30 mL)
  5. customThe solid was recrystallized from acetone/MeOH (2:1)

Sources & evidence

ORD record
ord-b1059b42da564c0eb250ee7211cf5cda
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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