Sodium Carbonate → HCID 90031368, compound

HRID 531569Notes

Reaction equation

HRID 531569 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][N:20]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[CH2:19][CH2:18]4)=[CH:13][CH:12]=3)[CH:9]=2)[N:4]([S:28]([C:31]2[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=2)(=[O:30])=[O:29])[CH:3]=1.[F:38][C:39]1[CH:40]=[C:41]([CH:59]=[CH:60][CH:61]=1)[CH2:42][N:43]1[C:47]([CH3:48])=[C:46](B2OC(C)(C)C(C)(C)O2)[C:45]([CH3:58])=[N:44]1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1.C(O)C.O>[F:38][C:39]1[CH:40]=[C:41]([CH:59]=[CH:60][CH:61]=1)[CH2:42][N:43]1[C:47]([CH3:48])=[C:46]([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][N:20]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[CH2:19][CH2:18]5)=[CH:13][CH:12]=4)[CH:9]=3)[N:4]([S:28]([C:31]3[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[CH:3]=2)[C:45]([CH3:58])=[N:44]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 90064815HCID 90064815, compound2×

Product 1

HCID 90031368HCID 90031368, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-ii of intermediate 1, 2-(4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)-N,N-dimethylethanamine (intermediate 49) (150 mg, 0.485 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) (157 mg, 0.477 mmol) in sodium carbonate (76 mg, 0.716 mmol), PdCl2(dppf) (8.7 mg, 0.011 mmol), Toluene/ethanol/water (15/7.5/1.5 ml) to afford 192 mg yield % of the crude titled compound. MS: m/z=706.0 (M+1).

Workup

  1. customreaction conditions
  2. customto afford 192 mg

Sources & evidence

ORD record
ord-2a69cff4873e4e359a32873062aeace8
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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