Sodium Carbonate → HCID 58896987, compound

HRID 1409110Notes

Reaction equation

HRID 1409110 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.CC1(C)C(C)(C)OB([C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[N:23]([S:26]([C:29]4[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=4)(=[O:28])=[O:27])[CH:24]=[CH:25][C:18]=23)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:8][C:4]1[N:3]=[C:2]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[N:23]([S:26]([C:29]4[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=4)(=[O:27])=[O:28])[CH:24]=[CH:25][C:18]=23)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 6394382-Bromo-6-fluoropyridineHCID 497589261-Tosyl-1H-pyrrolo(2,3-B)pyridine-4-boronic acid pinacol ester

Product 1

HCID 58896987HCID 58896987, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 20 mL microwave tube, 2-Bromo-6-fluoropyridine (L) (682 mg, 3.3 mmol, 1.2 equiv.), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (B)(1.1 g, 2.8 mmol, 1 equiv.) and Pd(PPh3)4 (323 mg, 0.28 mmol), 0.1 equiv.) were suspended in a mixture of DME (10 mL) and aqueous Na2CO3 2M (3 mL). The container was sealed and the reaction mixture was exposed to microwave irradiation for 30 min at 160° C. The resulting mixture was diluted in ethyl acetate, washed with water and dried over anhydrous Na2SO4. The crude material was purified by flash chromatography on silica gel, eluting with hexanes/ethyl acetate mixtures (90:10 to 60:40). The title compound J was isolated as a pale yellow solid (2.1 g, 50%).

Workup

  1. customThe container was sealed
  2. customirradiation for 30 min at 160° C
  3. washwashed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe crude material was purified by flash chromatography on silica gel
  6. washeluting with hexanes/ethyl acetate mixtures (90:10 to 60:40)

Sources & evidence

ORD record
ord-e48bd947ca6846f395da73726199c45e
Source dataset
uspto-grants-2014_12
Patent number
US08921376B2

Reaction notes

Loading…