1-Tosyl-1H-pyrrolo(2,3-B)pyridine-4-boronic acid pinacol ester → HCID 68194696, compound

HRID 2169618Notes

Reaction equation

HRID 2169618 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[N:15]([S:18]([C:21]4[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=4)(=[O:20])=[O:19])[CH:16]=[CH:17][C:10]=23)O1.Cl[C:30]1[N:39]=[CH:38][C:37]2[NH:36][CH2:35][CH:34]3[CH2:40][O:41][CH2:42][CH2:43][N:33]3[C:32]=2[N:31]=1>O1CCOCC1.C([O-])(O)=O.[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]>[S:18]([N:15]1[C:11]2=[N:12][CH:13]=[CH:14][C:9]([C:30]3[N:39]=[CH:38][C:37]4[NH:36][CH2:35][CH:34]5[CH2:40][O:41][CH2:42][CH2:43][N:33]5[C:32]=4[N:31]=3)=[C:10]2[CH:17]=[CH:16]1)([C:21]1[CH:22]=[CH:23][C:24]([CH3:25])=[CH:26][CH:27]=1)(=[O:19])=[O:20]

Participants

6

Reactant 2

HCID 497589261-Tosyl-1H-pyrrolo(2,3-B)pyridine-4-boronic acid pinacol esterHCID 86670087HCID 86670087, compound

Product 1

HCID 68194696HCID 68194696, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The title compound was prepared in a manner similar to EXAMPLE 2 using 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (PREPARATION x2, 527 mg, 1.324 mmol), 2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (150 mg, 0.662 mmol), and PdCl2(dppf) (38.7 mg, 0.053 mmol) in dioxane (3.5 mL) and aqueous saturated NaHCO3 (0.8 mL).

Sources & evidence

ORD record
ord-d354a8d97faf4402afbf36174cfceb23
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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