Sodium Carbonate → HCID 86621902, compound

HRID 1027898Notes

Reaction equation

HRID 1027898 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:26][CH:25]3[CH:20]([N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:23][CH2:24]3)[CH2:19]2)[C:5]2[CH2:12][CH2:11][O:10][C:9]3[CH:13]=[C:14](I)[CH:15]=[CH:16][C:8]=3[C:6]=2[N:7]=1.[C:34]1(B(O)O)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C(Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:26][CH:25]3[CH:20]([N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:23][CH2:24]3)[CH2:19]2)[C:5]2[CH2:12][CH2:11][O:10][C:9]3[CH:13]=[C:14]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH:15]=[CH:16][C:8]=3[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86621901HCID 86621901, compound

Product 1

HCID 86621902HCID 86621902, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

The product from Example 102A (32 mg, 0.057 mmol) was treated with phenylboronic acid (10 mg, 0.085 mmol), Pd(PPh)4 (6.6 mg, 5.7 μmol), and 2 M Na2CO3 (63 μl, 0.12 mmol) in 1,2-dimethoxyethane (170 μl), heated overnight at 90° C., cooled, diluted with CH2Cl2 (25 mL) and washed with 1 M NaOH (10 mL). The layers were separated and the aqueous was extracted with CH2Cl2 (25 mL). The combined CH2Cl2 layers were dried (MgSO4), filtered, concentrated and purified by chromatography on silica gel eluting with a gradient of 5:1 to 1:2 hexane:EtOAc to provide the title compound. 1H NMR (CDCl3) δ 1.32-1.46 (m, 2H), 1.49 (s, 9H), 1.52-1.82 (m, 3H), 2.15-2.28 (m, 1H), 2.64-2.89 (m, 3H), 3.35 (d, J=10.5 Hz, 1H), 3.54 (t, J=9.2 Hz, 1H), 3.72 (t, J=10.0 Hz, 1H), 3.87 (dd, J=10.7, 5.6 Hz, 1H), 4.00-4.09 (m, 1H), 4.72 (s, 3H), 4.72 (s, 2H), 7.32-7.40 (m, 1H), 7.41-7.50 (m, 3H), 7.61-7.66 (m, 2H), 8.14 (d, J=8.1 Hz, 1H); MS (M+H)+ m/z at 514.

Workup

  1. temperaturecooled
  2. washwashed with 1 M NaOH (10 mL)
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with CH2Cl2 (25 mL)
  5. dry with materialThe combined CH2Cl2 layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by chromatography on silica gel eluting with a gradient of 5:1 to 1:2 hexane

Sources & evidence

ORD record
ord-49803e7c80b241e38bf8ea0869deb721
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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