3-(Methylsulfonyl)phenylboronic acid → HCID 24969132, compound

HRID 2098866Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9](I)=[CH:8][C:6]=2[N:7]=1.[CH3:18][S:19]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)(=[O:21])=[O:20].CC1(C)C(C)(C)OB([C:39]2[CH:40]=[C:41]3[CH:47]=[CH:46][NH:45][C:42]3=[N:43][CH:44]=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>[CH3:18][S:19]([C:22]1[CH:23]=[C:24]([C:9]2[S:10][C:5]3[C:4]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][CH2:13]4)=[N:3][C:2]([C:39]4[CH:40]=[C:41]5[CH:47]=[CH:46][NH:45][C:42]5=[N:43][CH:44]=4)=[N:7][C:6]=3[CH:8]=2)[CH:25]=[CH:26][CH:27]=1)(=[O:21])=[O:20]

Participants

Conditions

Temperature: 150 °C

Procedure

2-Chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine 19 from Example 12 (0.2 g, 0.6 mmol), 3-(methylsulfonyl)phenylboronic acid (120 mg, 0.6 mmol), and bis(triphenylphosphine)palladium(II) dichloride (20 mg, 30 μmol) in 1M aqueous Na2CO3 (1 mL) and acetonitrile (1 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 (210 mg, 0.87 mmol) and bis(triphenylphosphine)palladium(II) dichloride (20 mg, 30 μmol) were added and the 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 418 after reverse phase HPLC purification (40 mg). MS (Q1) 492 (M)+

Workup

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

Sources & evidence

ORD record: ord-b02435d1809943d685111c753308912a
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450315B2

Reaction notes

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