Sodium Carbonate → HCID 90031536, compound

HRID 531579Notes

Reaction equation

HRID 531579 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[C:22]4[C:28](I)=[C:27]([CH:30]5[CH2:32][CH2:31]5)[N:26]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:23]4=[N:24][CH:25]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:40][C:41]1[CH:42]=[C:43]([CH:61]=[CH:62][CH:63]=1)[CH2:44][N:45]1[C:49]([CH3:50])=[C:48](B2OC(C)(C)C(C)(C)O2)[C:47]([CH3:60])=[N:46]1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[C:22]4[C:28]([C:48]5[C:47]([CH3:60])=[N:46][N:45]([CH2:44][C:43]6[CH:61]=[CH:62][CH:63]=[C:41]([F:40])[CH:42]=6)[C:49]=5[CH3:50])=[C:27]([CH:30]5[CH2:32][CH2:31]5)[N:26]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:23]4=[N:24][CH:25]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

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 90031009HCID 90031009, compound2×

Product 1

HCID 90031536HCID 90031536, compoundYield 178.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-1, tert-butyl 5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-2-cyclopropyl-3-iodo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (Intermediate 35) (50 mg, 0.07763 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) (30 mg, 0.08540 mmol) in sodium carbonate (25 mg, 0.2329 mmol), Pd(PPh3)4 (5 mg, 0.00388 mmol) and DME/water (5/1 ml) to afford 100 mg of the crude product which was taken as such for next reaction. MS: m/z=721.0 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-916bfd2fd93d4a9990b00b013ed227ee
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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