Phenylboronic Acid → HCID 24969129, compound

HRID 2098868Notes

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.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[C:38]3[CH:44]=[CH:43][NH:42][C:39]3=[N:40][CH:41]=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:36]3[CH:37]=[C:38]4[CH:44]=[CH:43][NH:42][C:39]4=[N:40][CH:41]=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:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 150 °C

Procedure

2-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine from Example 12 (0.2 g, 0.5 mmol), phenylboronic acid (60 mg, 0.5 mmol), and bis(triphenylphosphine)palladium(II) dichloride (18 mg, 25 μmol) in 1 M 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 (180 mg, 0.75 mmol) and bis(triphenylphosphine)palladium(II) dichloride (13 mg, 20 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 420 after reverse phase HPLC purification (57 mg). MS (Q1) 428 (M)+

Workup

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

Sources & evidence

ORD record: ord-59b5bc47c46a4367a64f26efbe690858
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450315B2

Reaction notes

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