Sodium Carbonate → HCID 57725593, compound

HRID 1922268Notes

Reaction equation

HRID 1922268 reaction equation
Br[C:2]1[C:10]2[S:9][C:8]([NH:11][C@@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]3[OH:18])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:19].[C:20]([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[OH:18][C@@H:13]1[CH2:14][CH2:15][CH2:16][CH2:17][C@H:12]1[NH:11][C:8]1[S:9][C:10]2[C:2]([CH3:20])=[C:3]([OH:19])[CH:4]=[CH:5][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 57725507HCID 57725507, compound

Product 1

HCID 57725593HCID 57725593, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To the solution of 7-bromo-2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-ol (117 mg, 0.34 mmol, 1.0 eq) in 1 mL DMF in a microwave vial was added trimethylboraxine (128 mg, 1.02 mmol, 3.0 eq), Pd(Cl2)dPPf (27 mg, 0.034 mmol, 0.1 eq) and 1 mL of 2M Na2CO3 solution at room temperature. Thereafter, the reaction mixture was heated in the microwave at 120° C. for 15 minutes. The reaction was quenched with saturated NaHCO3 solution (25 ml) and the aqueous phase extracted with ethyl acetate (50 mL×3), combined organic layers dried over Na2SO4, filtered and condensed under reduced pressure. Purification over ISCO using a gradient of 0%-18% methanol-DCM gave 17 mg of product as brownish powder in 17% yield. LC/MS (m/z) [279.1] (MH+)

Workup

  1. customThe reaction was quenched with saturated NaHCO3 solution (25 ml)
  2. extractionthe aqueous phase extracted with ethyl acetate (50 mL×3)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customcondensed under reduced pressure
  6. customPurification over ISCO

Sources & evidence

ORD record
ord-f99e4ec90f4f47afb245d1e62663addb
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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