Sodium Carbonate → HCID 131735684, compound

HRID 531879Notes

Reaction equation

HRID 531879 reaction equation
[F:1][C:2]1[C:3]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[N:4][CH:5]=[C:6]([C:8]2[CH:9]=[C:10]3[C:16](I)=[CH:15][N:14]([S:18]([C:21]4[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:11]3=[N:12][CH:13]=2)[CH:7]=1.[F:36][C:37]1[CH:38]=[C:39]([CH:55]=[CH:56][CH:57]=1)[CH2:40][N:41]1[CH:45]=[C:44](B2OC(C)(C)C(C)(C)O2)[CH:43]=[N:42]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.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>[F:1][C:2]1[C:3]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[N:4][CH:5]=[C:6]([C:8]2[CH:9]=[C:10]3[C:16]([C:44]4[CH:43]=[N:42][N:41]([CH2:40][C:39]5[CH:55]=[CH:56][CH:57]=[C:37]([F:36])[CH:38]=5)[CH:45]=4)=[CH:15][N:14]([S:18]([C:21]4[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:11]3=[N:12][CH:13]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 691327261-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×HCID 118535216HCID 118535216, compound2×

Product 1

HCID 131735684HCID 131735684, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-i of example-1, tert-butyl (3-fluoro-5-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)carbamate (intermediate 66T) (150 mg, 0.24 mmol) was coupled with 1-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 11) (82 mg, 0.27 mmol) using Pd(PPh3)2Cl2 (8 mg, 0.012 mol) and sodium carbonate (76 mg, 0.72 mmol) in toluene/ethanol/water (10/10/2 mL) to afford 122 mg (crude) of the titled compound. MS: m/z=657.2 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-5860978123234e97990f58649ec388c8
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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