Potassium Phosphate, Tribasic → HCID 67959633, compound

HRID 1529449Notes

Reaction equation

HRID 1529449 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[C:14](B3OC(C)(C)C(C)(C)O3)=[CH:15][N:16]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:11]2=[CH:10][CH:9]=1.Cl[C:37]1[N:38]=[N:39][CH:40]=[C:41]([O:43][CH3:44])[CH:42]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C(Cl)Cl.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[C:14]([C:37]3[N:38]=[N:39][CH:40]=[C:41]([O:43][CH3:44])[CH:42]=3)=[CH:15][N:16]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:18])=[O:19])[C:11]2=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 109756123-Chloro-5-methoxypyridazineHCID 67959950HCID 67959950, compound

Product 1

HCID 67959633HCID 67959633, compoundYield 16.3%

Reagents, catalysts & solvents 3

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)CatalystHCID 6344DichloromethaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
105 °C

Procedure

A glass microwave reaction vessel was charged with 5-(2-fluorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[3,2-b]pyridine (102 mg, 0.208 mmol) and 3-chloro-5-methoxypyridazine (30 mg, 0.208 mmol) in p-dioxane/H2O (4:1, 1.5 mL) followed by potassium phosphate (88 mg, 0.415 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(ii) (7.35 mg, 10.38 μmol). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 105° C. for 1 h. The mixture was diluted with DCM and washed with water. The organic layer was dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 10-35% EtOAc in Hex) to give 5-(2-fluorophenyl)-3-(5-methoxypyridazin-3-yl)-1-tosyl-1H-pyrrolo[3,2-b]pyridine (16 mg, 0.034 mmol, 16.25% yield) as a brown solid. MS (ESI, pos. ion) m/z: 475.0 (M+1).

Workup

  1. customA glass microwave reaction vessel
  2. washwashed with water
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel chromatography (eluting with 10-35% EtOAc in Hex)

Sources & evidence

ORD record
ord-ed38faef08044d1dac92e4f446ba3bc7
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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