Water → HCID 57585119, compound

HRID 2077614Notes

Reaction equation

HRID 2077614 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:9][S:10]([C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:21][NH:22][C:23]1[S:24][C:25]2[CH:31]=[C:30](B3OC(C)(C)C(C)(C)O3)[CH:29]=[CH:28][C:26]=2[N:27]=1.C(=O)([O-])[O-].[K+].[K+].O>COCCOC>[Cl:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:13]=1[S:10]([NH:9][C:4]1[C:5]([Cl:8])=[N:6][CH:7]=[C:2]([C:30]2[CH:29]=[CH:28][C:26]3[N:27]=[C:23]([NH:22][CH3:21])[S:24][C:25]=3[CH:31]=2)[CH:3]=1)(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 58279591N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-amineHCID 86628002HCID 86628002, compound

Product 1

HCID 57585119HCID 57585119, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

N-(5-bromo-2-chloropyridin-3-yl)-2-chloro-6-methylbenzenesulfonamide (210 mg, 0.530 mmol), N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-amine (101.6 mg, 0.350 mmol), potassium carbonate (250 mg, 1.81 mmol), and Pd(dppf) Cl2*DCM complex (62.6 mg, 0.0768 mmol) were suspended in DME (2.0 ml) and water (0.5) ml. The reaction flask was fit with a reflux condensor and placed in a preheated oil bath (100° C.) and stirred under nitrogen for 1 hour. The reaction was cooled to room temperature, and the aqueous phase was removed via pipette. The reaction was then concentrated and filtered through a silica gel plug with 5:1 to 3:1 DCM/2 N ammonia in MeOH. The filtrate was concentrated and purified on HPLC (10% to 100% MeCN/water with 0.1% TFA over 30 minutes) to afford 2-chloro-N-(2-chloro-5-(2-(methylamino)benzo[d]thiazol-6-yl)pyridin-3-yl)-6-methylbenzenesulfonamide (35.6 mg, 21% yield). MS (ESI pos. ion) m/z: 479 (MH+). Calc'd exact mass for C20H16Cl2N4O2S2: 478.

Workup

  1. customplaced in a preheated oil bath
  2. temperatureThe reaction was cooled to room temperature
  3. customthe aqueous phase was removed via pipette
  4. concentrationThe reaction was then concentrated
  5. filtrationfiltered through a silica gel plug with 5:1 to 3:1 DCM/2 N ammonia in MeOH
  6. concentrationThe filtrate was concentrated
  7. custompurified on HPLC (10% to 100% MeCN/water with 0.1% TFA over 30 minutes)

Sources & evidence

ORD record
ord-4ea1923b236e423288d7b73b6bb33e96
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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