Potassium Phosphate, Tribasic → HCID 90030845, compound

HRID 531841Notes

Reaction equation

HRID 531841 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:12]=3)=[CH:9][N:8]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:5]2=[N:6][CH:7]=1.[F:34][C:35]1[CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH:38]=[CH:37][C:36]=1[C:50]1[CH2:55][CH2:54][N:53]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:52][CH:51]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:34][C:35]1[CH:40]=[C:39]([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=5)[N:12]=4)=[CH:9][N:8]([S:24]([C:27]4[CH:28]=[CH:29][C:30]([CH3:31])=[CH:32][CH:33]=4)(=[O:26])=[O:25])[C:5]3=[N:6][CH:7]=2)[CH:38]=[CH:37][C:36]=1[C:50]1[CH2:55][CH2:54][N:53]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:52][CH:51]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 90031152tert-butyl 4-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate2×HCID 900648255-bromo-3-(1-phenethyl-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine2×

Product 1

HCID 90030845HCID 90030845, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Using similar reaction conditions as described in step-i of example-1, 5-bromo-3-(1-phenethyl-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (intermediate 63A) (160 mg, 0.307 mmol) was coupled with tert-butyl 4-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (intermediate 70) (307 mg, 0.769 mmol) using potassium phosphate (195 mg, 0.918 mmol), tricyclohexyl phosphine (13 mg, 0.046 mmol) and Pd2(dba)3 (28 mg, 0.030 mmol) in dioxane/water (15/3 ml) to afford 126 mg (57.2% yield) of the pure product after column purification using 35% ethyl acetate in hexane as eluent. MS: m/z=718.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-fb8ef6a4464245c085d7f98023ae842d
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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