3-(Methylsulfonyl)phenylboronic acid → HCID 59593102, compound

HRID 2262249Notes

Reaction equation

HRID 2262249 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:48]=[CH:47][CH:46]=[C:45]3[C:41]=2[CH:42]=[N:43][NH:44]3)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>[NH:44]1[C:45]2[C:41](=[C:40]([C:2]3[N:3]=[C:4]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)[C:5]4[S:10][C:9]([C:27]5[CH:26]=[CH:25][CH:24]=[C:23]([S:20]([CH3:19])(=[O:22])=[O:21])[CH:28]=5)=[C:8]([CH3:12])[C:6]=4[N:7]=3)[CH:48]=[CH:47][CH:46]=2)[CH:42]=[N:43]1

Participants

7

Reactant 3

HCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 595928802-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine

Product 1

HCID 59593102HCID 59593102, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 6342AcetonitrileSolvent2×HCID 10340Sodium CarbonateSolvent2×

Conditions

Temperature
150 °C

Procedure

2-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine from Example 12 (0.6 g, 1.5 mmol), 3-(methylsulfonyl)phenylboronic acid (0.3 g, 1.5 mmol), and bis(triphenylphosphine)palladium(II) dichloride (53 mg, 80 μmol) in 1 M aqueous Na2CO3 (3 mL) and acetonitrile (3 mL) were heated to 100° C. in a sealed microwave reactor for 10 min. Upon completion the organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organics were concentrated in vacuo. A portion of the residue (0.38 mmol) was dissolved in 1 M Na2CO3 (1.5 mL) and CH3CN (1.5 mL) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)1H-indazole 7 (0.2 g, 0.8 mmol) and bis(triphenylphosphine)palladium(II) dichloride (13 mg, 20 μmol) were added into the same pot. The reaction mixture was heated to 150° C. in a sealed microwave reactor for 30 min. The mixture was extracted with EtOAc and CH2Cl2. The combined organics were concentrated to yield 360 after reverse phase HPLC purification (90 mg). MS (Q1) 506 (M)+

Workup

  1. customUpon completion the organic layer was separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. concentrationThe combined organics were concentrated in vacuo
  4. extractionThe mixture was extracted with EtOAc and CH2Cl2
  5. concentrationThe combined organics were concentrated

Sources & evidence

ORD record
ord-4dba367e3658408c9a3a59be033b8622
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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