Sodium Carbonate → 5-bromo-3-(1-(4-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.[F:22][C:23]1[CH:43]=[CH:42][C:26]([CH2:27][N:28]2[CH:32]=[C:31](B3OC(C)(C)C(C)(C)O3)[CH:30]=[N:29]2)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C1(C)C=CC=CC=1.C(O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:31]3[CH:30]=[N:29][N:28]([CH2:27][C:26]4[CH:42]=[CH:43][C:23]([F:22])=[CH:24][CH:25]=4)[CH:32]=3)=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Using similar reaction conditions as described in step-i of example-1,5-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (Intermediate 1) (700 mg, 1.46 mmol) was coupled with 1-(4-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 7) (554 mg, 1.83 mmol) in sodium carbonate (466 mg, 4.4 mmol), bis(triphenylphosphine) palladium(ii)dichloride (51 mg, 0.073 mmol) and toluene/ethanol/water (20/8/2 ml) to afford 300 mg (38.9% yield) of the pure product after column purification using 20% ethyl acetate in hexane as eluent. MS: m/z=526.7 (M+1).
Workup
- customreaction conditions
Sources & evidence
- ORD record
- ord-3efae03a969d4db79712a6b1f29489c5
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09353107B2
Reaction notes
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