3-(Methylsulfonyl)phenylboronic acid → HCID 59592895, compound

HRID 2262278Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9](I)=[C:8]([CH3:12])[C:6]=2[N:7]=1.[CH3:19][S:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)(=[O:22])=[O:21].CC1(C)C(C)(C)OB([C:40]2[CH:41]=[C:42]3[CH:48]=[CH:47][NH:46][C:43]3=[N:44][CH:45]=2)O1>C([O-])([O-])=O.[Na+].[Na+].C(#N)C.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>[CH3:12][C:8]1[C:6]2[N:7]=[C:2]([C:40]3[CH:41]=[C:42]4[CH:48]=[CH:47][NH:46][C:43]4=[N:44][CH:45]=3)[N:3]=[C:4]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[C:5]=2[S:10][C:9]=1[C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([S:20]([CH3:19])(=[O:22])=[O:21])[CH:28]=1

Participants

Conditions

Temperature: 150 °C

Procedure

2-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine from Example 12 (0.3 g, 0.8 mmol), 3-(methylsulfonyl)phenylboronic acid (0.3 g, 1.5 mmol), and bis(triphenylphosphine)palladium(II) dichloride (30 mg, 40 μmol) in 1 M aqueous Na2CO3 (1.5 mL) and acetonitrile (1.5 mL) were heated to 100° C. in a sealed microwave reactor for 10 min. Upon completion, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (0.4 g, 1.7 mmol), and bis(triphenylphosphine)palladium(II) dichloride (30 mg, 40 μmol) were added into the same pot. The reaction mixture was heated to 150° C. in a sealed microwave reactor for 20 min. The mixture was extracted with EtOAc and CH2Cl2. The combined organics were concentrated to yield 395 after reverse phase HPLC purification (82 mg). MS (Q1) 506 (M)+

Workup

extractionThe mixture was extracted with EtOAc and CH2Cl2
concentrationThe combined organics were concentrated

Sources & evidence

ORD record: ord-2b765877e7f24a0db96f8934523a5db4
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846929B2

Reaction notes

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