Sodium Carbonate → tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

HRID 531596Notes

Reaction equation

HRID 531596 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([C:21]2[CH:22]=[C:23]3[C:29](I)=[CH:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:24]3=[N:25][CH:26]=2)[CH:16]=N[C:18]=1[O:19][CH3:20])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:46]2[CH:47]=[N:48][N:49]([CH2:51][C:52]3[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=3)[CH:50]=2)O1.[C:59](=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>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([C:21]2[CH:22]=[C:23]3[C:29]([C:46]4[CH:47]=[N:48][N:49]([CH2:51][C:52]5[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=5)[CH:50]=4)=[CH:28][N:27]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[C:24]3=[N:25][CH:26]=2)[CH:16]=[CH:59][C:18]=1[O:19][CH3:20])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 179991853-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine2×HCID 90064817tert-butyl 5-(5-(N-(tert-butoxycarbonyl)methylsulfonamido)-6-methoxypyridin-3-yl)-3-iodo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate2×

Product 1

HCID 131735669tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylateYield 38.2%

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 5-(5-(N-(tert-butoxycarbonyl)methylsulfonamido)-6-methoxypyridin-3-yl)-3-iodo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (intermediate 66P) (150 mg, 0.233 mmol) was coupled with 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine (intermediate 64) (73 mg, 0.256 mmol) using Pd(PPh3)2Cl2 (9 mg, 0.0116 mol) and sodium carbonate (74 mg, 0.699 mmol) in toluene/ethanol/water (3/3/2 ml) to afford 60 mg (38% yield) of the titled compound after purification by column (Silica gel 60/120) using 30% ethyl acetate in hexane as eluent. MS: m/z=675.1 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-761a3e6ea3804a69b0df4462de6a5a00
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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