Sodium Carbonate → HCID 118524077, compound

HRID 531548Notes

Reaction equation

HRID 531548 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:13][CH:12]=3)[CH:9]=2)[N:4]([S:23]([C:26]2[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:3]=1.[F:33][C:34]1[CH:35]=[C:36]([CH:54]=[CH:55][CH:56]=1)[CH2:37][N:38]1[C:42]([CH3:43])=[C:41](B2OC(C)(C)C(C)(C)O2)[C:40]([CH3:53])=[N:39]1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.C(O)C.O>[F:33][C:34]1[CH:35]=[C:36]([CH:54]=[CH:55][CH:56]=1)[CH2:37][N:38]1[C:42]([CH3:43])=[C:41]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:16]=[CH:15][C:14]([N:17]5[CH2:22][CH2:21][O:20][CH2:19][CH2:18]5)=[CH:13][CH:12]=4)[CH:9]=3)[N:4]([S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:3]=2)[C:40]([CH3:53])=[N:39]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 900306711-(3-Fluoro-benzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole2×HCID 90064858HCID 90064858, compound2×

Product 1

HCID 118524077HCID 118524077, compoundYield 58.82%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-1, 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)morpholine (intermediate 43) (150 mg, 0.268 mmol) was coupled with 1-(3-fluorobenzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 16) (133 mg, 0.402 mmol) in sodium carbonate (86 mg, 0.805 mmol), Pd(PPh3)2Cl2 (10 mg, 0.0134 mmol), Toluene/ethanol/water (5/5/5 ml) to afford 100 mg (58.82% yield) of titled compound. MS: m/z=636.1 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-7c4c9fa23e494782b54719e0e8290c2a
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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